Methanol → 4-(3,4-Dimethoxyphenyl)-2-(2-hydroxyethyl)-6,7-dimethoxyquinazoline

HRID 266121Notes

Reaction equation

HRID 266121 reaction equation
CO.[CH3:3][O:4][C:5]1[CH:6]=[C:7]([C:13]2[C:22]3[C:17](=[CH:18][C:19]([O:25][CH3:26])=[C:20]([O:23][CH3:24])[CH:21]=3)[N:16]=[C:15]([CH2:27][C:28](OC)=[O:29])[N:14]=2)[CH:8]=[CH:9][C:10]=1[O:11][CH3:12].[BH4-].[Na+].O1CCCC1>O>[CH3:3][O:4][C:5]1[CH:6]=[C:7]([C:13]2[C:22]3[C:17](=[CH:18][C:19]([O:25][CH3:26])=[C:20]([O:23][CH3:24])[CH:21]=3)[N:16]=[C:15]([CH2:27][CH2:28][OH:29])[N:14]=2)[CH:8]=[CH:9][C:10]=1[O:11][CH3:12]

Participants

6

Reactant 4

HCID 887MethanolHCID 8028TetrahydrofuranHCID 4311764Sodium borohydrideHCID 212240726,7-Dimethoxy-4-(3,4-dimethoxyphenyl)quinazoline-2-acetic acid methyl ester

Product 1

HCID 220975944-(3,4-Dimethoxyphenyl)-2-(2-hydroxyethyl)-6,7-dimethoxyquinazolineYield 81%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Methanol (15 ml) was added dropwise to a mixture of methyl 4-(3,4-dimethoxyphenyl)-6,7-dimethoxyquinazoline-2-acetate (4.0 g), sodium borohydride (1.9 g) and tetrahydrofuran (80 ml) under reflux. The mixture was stirred under reflux for 2 hours, and then poured into water, and extracted with ethyl acetate. The ethyl acetate layer was washed with water and dried over magnesium sulfate. Evaporation of the solvent gave 4-(3,4-dimethoxyphenyl)-2-(2-hydroxyethyl)-6,7-dimethoxyquinazoline (3.0 g, 81%). This was recrystallized from ethyl acetate. Colorless needles, mp. 165°-166° C.

Workup

  1. temperatureunder reflux
  2. temperatureunder reflux for 2 hours
  3. extractionextracted with ethyl acetate
  4. washThe ethyl acetate layer was washed with water
  5. dry with materialdried over magnesium sulfate
  6. customEvaporation of the solvent

Sources & evidence

ORD record
ord-be8bbc0e4b694cb4b8ea6509d2d11b45
Source dataset
uspto-grants-1997_07
Patent number
US05650410

Reaction notes

Loading…