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

HRID 1458930Notes

Reaction equation

HRID 1458930 reaction equation
CO.[CH3:3][O:4][C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][C:14]=1[O:15][CH3:16])[N:11]=[C:10]([CH2:17][C:18](OC)=[O:19])[N:9]=[C:8]2[C:22]1[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[C:24]([O:30][CH3:31])[CH:23]=1.[BH4-].[Na+].O1CCCC1>O>[CH3:3][O:4][C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][C:14]=1[O:15][CH3:16])[N:11]=[C:10]([CH2:17][CH2:18][OH:19])[N:9]=[C:8]2[C:22]1[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[C:24]([O:30][CH3:31])[CH:23]=1

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 under reflux to a mixture of methyl 6,7-dimethoxy-4-(3,4-dimethoxyphenyl)-quinazoline-2-acetate (4.0 g), sodium borohydride (1.9 g) and tetrahydrofuran (80 ml). The mixture was stirred under reflux for 2 hours, poured into water and extracted with ethyl acetate. The ethyl acetate layer was washed with water, dried over magnesium sulfate. The solvent was evaporated under reduced pressure to give 6,7-dimethoxy-4-(3,4-dimethoxyphenyl)-2-(2-hydroxyethyl)quinazoline (3.0 g, 81%) which was then recrystallized from ethyl acetate. Colorless needle crystals. mp. 165°-166° C.

Workup

  1. temperatureunder reflux for 2 hours
  2. extractionextracted with ethyl acetate
  3. washThe ethyl acetate layer was washed with water
  4. dry with materialdried over magnesium sulfate
  5. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-522738c713d74fb29cb05309b02f1e02
Source dataset
uspto-grants-1998_12
Patent number
US05852039

Reaction notes

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