2-甲氧基萘-1-醇

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

实验步骤: The formate of 2-methoxy-1-naphthol (J. E. Oatis, Jr., M. P. Russell, D. R. Knapp and T. Walle, J. Med. Chem. 1981, 24, 309) (7.23 g, 30.3 mmol), 2,4-diamino-5-hydroxymethylpyrimidine (4.35 g, 30.3 mmol), concentrated hydrochloric acid (4.2 mL) and glacial acetic acid (60 mL) were refluxed 2 hr. The resulting dark solution was evaporated to dryness and the residue dissolved in water and neutralized with ammonia. The resulting tan precipitate (5.2 g) was recrystallized from aqueous ethanol containing a slight excess of hydrochloric acid to give title compound as tan powder (2.83 g, 28%); mp ca. 290°-300° dec. Anal. Calcd for C16H16N4O2.HCl: C, 57.75; H, 5.15; N, 16.84; Cl, 10.65. Found: C, 57.62; H, 5.21; N, 16.79; Cl, 10.61. The resulting dark solution was evaporated to dryness the residue dissolved in water and neutralized with ammonia The resulting tan precipitate (5.2 g) was recrystallized from aqueous ethanol containing a slight excess of hydrochloric acid

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

实验步骤: The formate of 2-methoxy-1-naphthol (J. E. Oatis, Jr., M. P. Russell, D. R. Knapp and T. Walle, J. Med. Chem. 1981, 24, 309) (7.23 g, 30.3 mmol), 2,4-diamino-5-hydroxymethylpyrimidine (4.35 g, 30.3 mmol), concentrated hydrochloric acid (4.2 mL) and glacial acetic acid (60 mL) were refluxed 2 hr. The resulting dark solution was evaporated to dryness and the residue dissolved in water and neutralized with ammonia. The resulting tan precipitate (5.2 g) was recrystallized from aqueous ethanol containing a slight excess of hydrochloric acid to give title compound as tan powder (2.83 g, 28%); mp ca. 290°-300° dec. Anal. Calcd for C16H16N4O2.HCl: C, 57.75; H, 5.15; N, 16.84; Cl, 10.65. Found: C, 57.62; H, 5.21; N, 16.79; Cl, 10.61. The resulting dark solution was evaporated to dryness the residue dissolved in water and neutralized with ammonia The resulting tan precipitate (5.2 g) was recrystallized from aqueous ethanol containing a slight excess of hydrochloric acid

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

实验步骤: The formate of 2-methoxy-1-naphthol (J. E. Oatis, Jr., M. P. Russell, D. R. Knapp and T. Walle, J. Med. Chem. 1981, 24, 309) (7.23 g, 30.3 mmol), 2,4-diamino-5-hydroxymethylpyrimidine (4.35 g, 30.3 mmol), concentrated hydrochloric acid (4.2 mL) and glacial acetic acid (60 mL) were refluxed 2 hr. The resulting dark solution was evaporated to dryness and the residue dissolved in water and neutralized with ammonia. The resulting tan precipitate (5.2 g) was recrystallized from aqueous ethanol containing a slight excess of hydrochloric acid to give title compound as tan powder (2.83 g, 28%); mp ca. 290°-300° dec. Anal. Calcd for C16H16N4O2.HCl: C, 57.75; H, 5.15; N, 16.84; Cl, 10.65. Found: C, 57.62; N, 5.21; N, 16.79; Cl, 10.61. The resulting dark solution was evaporated to dryness the residue dissolved in water and neutralized with ammonia The resulting tan precipitate (5.2 g) was recrystallized from aqueous ethanol containing a slight excess of hydrochloric acid

反应条件: temp:40.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: A mixture of 5-hydroxy-6-methoxynaphthalene (2.10 g, 12.1 mmole), cesium carbonate (19.7 g, 60.5 mmole), N,N-dimethylformamide (12 ml) and 2-bromopropane (3.50 ml, 36.9 mmole) was stirred in a 40° C. oil bath overnight. The reaction mixture was filtered and the solid residue was rinsed thoroughly with ethyl ether. The filtrate and the washings were combined and concentrated in vacuo to remove most of the solvents. The brown residue was partitioned between water and ether and the layers were separated. The ether layer was washed with water. The combined aqueous layers were back extracted with ether. The ether extracts were combined, washed with brine and dried over sodium sulfate. Filtration and concentration gave a crude which was purified by column chromatography (2.5→5% ethyl acetate/hexanes) to give 1-isopropoxy-6-methoxynaphthalene (2.23 g, 86% yield) as a light brown oil. 1H NMR (CDCl3) δ 8.17 (1H, d, phenyl), 7.05-7.38 (4H, m, phenyl), 6.72 (1H, dd, phenyl), 4.73 (1H, m, CH of iPr), 3.92 (3H, s, OCH3), 1.42 (6H, d, 2 CH3 of iPr). Step 3: The reaction mixture was filtered the solid residue was rinsed thoroughly with ethyl ether concentrated in vacuo to remove most of the solvents The brown residue was partitioned between water and ether the layers were separated The ether layer was washed with water The combined aqueous layers were back extracted with ether washed with brine dried over sodium sulfate Filtration and concentration gave a crude which was purified by column chromatography (2.5→5% ethyl acetate/hexanes)

反应条件: temp:40.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: A mixture of 5-hydroxy-6-methoxynaphthalene (2.10 g, 12.1 mmole), cesium carbonate (19.7 g, 60.5 mmole), N,N-dimethylformamide (12 ml) and 2-bromopropane (3.50 ml, 36.9 mmole) was stirred in a 40° C. oil bath overnight. The reaction mixture was filtered and the solid residue was rinsed thoroughly with ethyl ether. The filtrate and the washings were combined and concentrated in vacuo to remove most of the solvents. The brown residue was partitioned between water and ether and the layers were separated. The ether layer was washed with water. The combined aqueous layers were back extracted with ether. The ether extracts were combined, washed with brine and dried over sodium sulfate. Filtration and concentration gave a crude which was purified by column chromatography (2.5→5% ethyl acetate/hexanes) to give 1-isopropoxy-6-methoxynaphthalene (2.23 g, 86% yield) as a light brown oil. 1H NMR (CDCl3) δ8.17 (1H, d, phenyl), 7.05-7.38 (4H, m, phenyl), 6.72 (1H, dd, phenyl), 4.73 (1H, m, CH of iPr), 3.92 (3H, s, OCH3), 1.42 (6H, d, 2 CH3 of iPr). The reaction mixture was filtered the solid residue was rinsed thoroughly with ethyl ether concentrated in vacuo to remove most of the solvents The brown residue was partitioned between water and ether the layers were separated The ether layer was washed with water The combined aqueous layers were back extracted with ether washed with brine dried over sodium sulfate Filtration and concentration gave a crude which was purified by column chromatography (2.5→5% ethyl acetate/hexanes)

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

实验步骤: The formate of 2-methoxy-1-naphthol (J. E. Oatis, Jr., M. P. Russell, D. R. Knapp and T. Walle, J. Med. Chem. 1981, 24, 309) (7.23 g, 30.3 mmol), 2,4-diamino-5-hydroxymethylpyrimidine (4.35 g, 30.3 mmol), concentrated hydrochloric acid (4.2 mL) and glacial acetic acid (60 mL) were refluxed 2 hr. The resulting dark solution was evaporated to dryness and the residue dissolved in water and neutralized with ammonia. The resulting tan precipitate (5.2 g) was recrystallized from aqueous ethanol containing a slight excess of hydrochloric acid to give title compound as tan powder (2.83 g, 28%); mp ca. 290°-300° dec. Anal. Calcd for C16H16N4O2.HCl: C, 57.75; H, 5.15; N, 16.84; Cl, 10.65. Found: C, 57.62; H, 5.21; N, 16.79; Cl, 10.61. The resulting dark solution was evaporated to dryness the residue dissolved in water and neutralized with ammonia The resulting tan precipitate (5.2 g) was recrystallized from aqueous ethanol containing a slight excess of hydrochloric acid