4-溴丁基硼酸

反应条件: temp:0.00; pressure:0.00; stir:

反应条件: temp:0.00; pressure:0.00; stir:

反应条件: temp:0.00; pressure:0.00; stir:

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: The title compound was synthesized in a similar manner as the compound of Example 1 with 2-amino-6-chloropurine (1.36 g, 8 mmol), 4-bromobutyl boronic acid (1.45 g, 8 mmol), and potassium carbonate (1.66 g, 12 mmol) in dimethylformamide (20 mL). Yield 56%; Wt. 1.2 g; mp 154°-156° C.; 1H NMR (DMSO-d6) 0.55-0.68 (t, B CH2), 1.20-1.32 (m, B CH2 CH2), 1.68-1.77 (m, B CH2 CH2 CH2), 4.00-4.08 (t, CH2 CH2 N), 6.85-6.92 (s, H2N C2 purine), 7.40-7.42 (s, (HO)2 B), 8.10-8.12 (s, H C8 purine). Electrospray Mass Spectrum (MH)+ (low resolution); Calcd. 270.09 (C9H13O2N5BCl); Found 270.10 (37 ppm).

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: The title compound was synthesized in a similar manner as the compound of Example 1 with 2-amino-6-chloropurine (1.36 g, 8 mmol), 4-bromobutyl boronic acid (1.45 g, 8 mmol), and potassium carbonate (1.66 g, 12 mmol) in dimethylformamide (20 mL). Yield 56%; Wt. 1.2 g; mp 154°-156° C.; 1H NMR (DMSO-d6) 0.55-0.68 (t, B CH2), 1.20-1.32 (m, B CH2 CH2), 1.68-1.77 (m, B CH2 CH2 CH2), 4.00-4.08 (t, CH2 CH2 N), 6.85-6.92 (s, H2N C2 purine), 7.40-7.42 (s, (HO)2 B), 8.10-8.12 (s, H C8 purine). Electrospray Mass Spectrum (MH)+ (low resolution); Calcd. 270.09 (C9H13O2N5BCl); Found 270.10 (37 ppm).

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: Sodium hydride (0.22 g, 7.2 mmol) was added to a solution of 6-chloropurine (0.93 g, 6.0 mmol) in dimethylformamide (20 mL) and stirred for 10 minutes. 4-Bromobutyl boronic acid (1.1 g, 6.0 mmol) in dimethylformamide (5 mL) was added to the reaction mixture and stirred at room temperature for 16 hours. After the removal of the dimethylformamide under high vacuum, the residue was purified by column chromatography (chloroform/methanol discontinuous gradient 95:5, 9:1) to yield 0.78 g of pure product. Yield 51%; mp 135°-138° C.; 1H NMR (DMSO-d6) 0.55-0.68 (t, B CH2), 1.22-1.35 (m, B CH2 CH2), 1.78-1.91 (m, B CH2 CH2 CH2), 4.26-4.32 (t, CH2 CH2 N), 7.40-7.42 (s, (HO)2 B), 8.68-8.70 (s, H C8 purine), 8.80-8.81 (s, H C2 purine). Elemental Analysis. (C9H12BO2N4Cl); Calcd. C, 42.47%; H, 4.75%; N, 22.02%; Found C, 42.48%; H, 4.80%; N, 22.06%. stirred at room temperature for 16 hours After the removal of the dimethylformamide under high vacuum the residue was purified by column chromatography (chloroform/methanol discontinuous gradient 95:5, 9:1)

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: Potassium carbonate (0.6 g, 4.4 mmol) was added to a solution of thymine (0.56 g, 4.4 mmol) in dimethylformamide (15 mL) and stirred for 30 minutes. To this reaction mixture, 4-bromobutyl boronic acid (0.4 g, 2.2 mmol) dissolved in dimethylformamide (5 mL) was added dropwise, and stirring was continued 2 days at room temperature. After the potassium carbonate was filtered, the dimethylformamide was evaporated under high vacuum. The residue was purified on a silica gel column eluting with a discontinuous gradient of chloroform/methanol (95:5, 85:15). The appropriate TLC-homogenous fractions were pooled and evaporated to give 0.22 g of pure product. Yield 44%; mp 130°-132° C.; 1H NMR (DMSO-d6) 0.55-0.68 (t, B CH2), 1.22-1.35 (m, B CH2 CH2), 1.42-1.60 (m, B CH2 CH2 CH2), 1.72-1.78 (s, CH3 C5 thymine), 3.52-3.63 (CH2 CH2 N), 7.40-7.43 (s, (HO)2 B), 7.48-7.51 (s, H C6 thymine), 11.12-11.18 (s, HN thymine). Elemental Analysis (C9H15BO4N2); Calcd. C, 47.82%; H, 6.69%; N, 12.40%; Found C, 47.71%; H, 6.72%; N, 12.35%. was added dropwise stirring was continued 2 days at room temperature After the potassium carbonate was filtered the dimethylformamide was evaporated under high vacuum The residue was purified on a silica gel column eluting with a discontinuous gradient of chloroform/methanol (95:5, 85:15) evaporated

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: Potassium carbonate (0.6 g, 4.4 mmol) was added to a solution of thymine (0.56 g, 4.4 mmol) in dimethylformamide (15 mL) and stirred for 30 minutes. To this reaction mixture, 4-bromobutyl boronic acid (0.4 g, 2.2 mmol) dissolved in dimethylformamide (5 mL) was added dropwise, and stirring was continued 2 days at room temperature. After the potassium carbonate was filtered, the dimethylformamide was evaporated under high vacuum. The residue was purified on a silica gel column eluting with a discontinuous gradient of chloroform/methanol (95:5, 85:15). The appropriate TLC-homogenous fractions were pooled and evaporated to give 0.22 g of pure product. Yield 44%; mp 130°-132° C.; 1H NMR (DMSO-d6) 0.55-0.68 (t, B CH2), 1.22-1.35 (m, B CH2 CH2), 1.42-1.60 (m, B CH2 CH2 CH2), 1.72-1.78 (s, CH3 C5 thymine), 3.52-3.63 (CH2 CH2 N), 7.40-7.43 (s, (HO)2 B), 7.48-7.51 (s, H C6 thymine), 11.12-11.18 (s, HN thymine). Elemental Analysis (C9H15BO4N2); Calcd. C, 47.82%; H, 6.69%; N, 12.40%; Found C, 47.71%; H, 6.72%; N, 12.35%. was added dropwise stirring was continued 2 days at room temperature After the potassium carbonate was filtered the dimethylformamide was evaporated under high vacuum The residue was purified on a silica gel column eluting with a discontinuous gradient of chloroform/methanol (95:5, 85:15) evaporated

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: The title compound was synthesized in a similar manner as the compound of Example 1 with 2-amino-6-chloropurine (1.36 g, 8 mmol), 4-bromobutyl boronic acid (1.45 g, 8 mmol), and potassium carbonate (1.66 g, 12 mmol) in dimethylformamide (20 mL). Yield 56%; Wt. 1.2 g; mp 154°-156° C.; 1H NMR (DMSO-d6) 0.55-0.68 (t, B CH2), 1.20-1.32 (m, B CH2 CH2), 1.68-1.77 (m, B CH2 CH2 CH2), 4.00-4.08 (t, CH2 CH2 N), 6.85-6.92 (s, H2N C2 purine), 7.40-7.42 (s, (HO)2 B), 8.10-8.12 (s, H C8 purine). Electrospray Mass Spectrum (MH)+ (low resolution); Calcd. 270.09 (C9H13O2N5BCl); Found 270.10 (37 ppm).

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: Sodium hydride (0.22 g, 7.2 mmol) was added to a solution of 6-chloropurine (0.93 g, 6.0 mmol) in dimethylformamide (20 mL) and stirred for 10 minutes. 4-Bromobutyl boronic acid (1.1 g, 6.0 mmol) in dimethylformamide (5 mL) was added to the reaction mixture and stirred at room temperature for 16 hours. After the removal of the dimethylformamide under high vacuum, the residue was purified by column chromatography (chloroform/methanol discontinuous gradient 95:5, 9:1) to yield 0.78 g of pure product. Yield 51%; mp 135°-138° C.; 1H NMR (DMSO-d6) 0.55-0.68 (t, B CH2), 1.22-1.35 (m, B CH2 CH2), 1.78-1.91 (m, B CH2 CH2 CH2), 4.26-4.32 (t, CH2 CH2 N), 7.40-7.42 (s, (HO)2 B), 8.68-8.70 (s, H C8 purine), 8.80-8.81 (s, H C2 purine). Elemental Analysis. (C9H12BO2N4Cl); Calcd. C, 42.47%; H, 4.75%; N, 22.02%; Found C, 42.48%; H, 4.80%; N, 22.06%. stirred at room temperature for 16 hours After the removal of the dimethylformamide under high vacuum the residue was purified by column chromatography (chloroform/methanol discontinuous gradient 95:5, 9:1)

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: Potassium carbonate (0.6 g, 4.4 mmol) was added to a solution of thymine (0.56 g, 4.4 mmol) in dimethylformamide (15 mL) and stirred for 30 minutes. To this reaction mixture, 4-bromobutyl boronic acid (0.4 g, 2.2 mmol) dissolved in dimethylformamide (5 mL) was added dropwise, and stirring was continued 2 days at room temperature. After the potassium carbonate was filtered, the dimethylformamide was evaporated under high vacuum. The residue was purified on a silica gel column eluting with a discontinuous gradient of chloroform/methanol (95:5, 85:15). The appropriate TLC-homogenous fractions were pooled and evaporated to give 0.22 g of pure product. Yield 44%; mp 130°-132° C.; 1H NMR (DMSO-d6) 0.55-0.68 (t, B CH2), 1.22-1.35 (m, B CH2 CH2), 1.42-1.60 (m, B CH2 CH2 CH2), 1.72-1.78 (s, CH3 C5 thymine), 3.52-3.63 (CH2 CH2 N), 7.40-7.43 (s, (HO)2 B), 7.48-7.51 (s, H C6 thymine), 11.12-11.18 (s, HN thymine). Elemental Analysis (C9H15BO4N2); Calcd. C, 47.82%; H, 6.69%; N, 12.40%; Found C, 47.71%; H, 6.72%; N, 12.35%. was added dropwise stirring was continued 2 days at room temperature After the potassium carbonate was filtered the dimethylformamide was evaporated under high vacuum The residue was purified on a silica gel column eluting with a discontinuous gradient of chloroform/methanol (95:5, 85:15) evaporated

反应条件: temp:0.00; pressure:0.00; stir: