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

HRID 964584Notes

Reaction equation

HRID 964584 reaction equation
C[O:2][C:3](=O)[CH2:4][C:5]1[N:14]=[C:13]([C:15]2[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[C:17]([O:23][CH3:24])[CH:16]=2)[C:12]2[C:7](=[CH:8][C:9]([O:28][CH3:29])=[C:10]([O:26][CH3:27])[C:11]=2C)[N:6]=1.[BH4-].[Na+].O1CCCC1.CO>O>[CH3:27][O:26][C:10]1[CH:11]=[C:12]2[C:7](=[CH:8][C:9]=1[O:28][CH3:29])[N:6]=[C:5]([CH2:4][CH2:3][OH:2])[N:14]=[C:13]2[C:15]1[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[C:17]([O:23][CH3:24])[CH:16]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 8028TetrahydrofuranHCID 4311764Sodium borohydrideHCID 57272645Methyl 6,7-dimethoxy-4-(3,4-dimethoxyphenyl)quinazoline-2-acetic acid methyl ester

Product 1

HCID 220975944-(3,4-Dimethoxyphenyl)-2-(2-hydroxyethyl)-6,7-dimethoxyquinazolineYield 83.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of methyl 6,7-dimethoxy-4-(3,4-dimethoxyphenyl)quinazoline-2-acetic acid methyl ester(4.0 g), sodium borohydride (1.9 g) and tetrahydrofuran (80 ml), methanol (15 ml) was added dropwise under continuous reflux, followed by refluxing for 2 hours. The reaction mixture was poured into water and extracted with ethyl acetate. The ethyl acetate layer was washed with water, dried (MgSO4) and concentrated under reduced pressure to yield 6,7-dimethoxy-4-(3,4-dimethoxyphenyl)-2-(2-hydroxyethyl) quinazoline (3.0 g, 81%). Recrystallization from ethyl acetate gave a colorless needle crystal having a melting point of 165° to 166° C.

Workup

  1. additionwas added dropwise under continuous reflux
  2. temperatureby refluxing for 2 hours
  3. extractionextracted with ethyl acetate
  4. washThe ethyl acetate layer was washed with water
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-d52a6034111d49d8ad79f8cf31a6b2d6
Source dataset
uspto-grants-1998_06
Patent number
US05770602

Reaction notes

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