Sodium borohydride → {4-[(3-Chloro-2-fluorophenyl)amino]-7-methoxyquinazolin-6-yl}methanol

HRID 1867718Notes

Reaction equation

HRID 1867718 reaction equation
[BH4-].[Na+].[Cl:3][C:4]1[C:5]([F:25])=[C:6]([NH:10][C:11]2[C:20]3[C:15](=[CH:16][C:17]([O:23][CH3:24])=[C:18]([CH:21]=[O:22])[CH:19]=3)[N:14]=[CH:13][N:12]=2)[CH:7]=[CH:8][CH:9]=1>CO>[Cl:3][C:4]1[C:5]([F:25])=[C:6]([NH:10][C:11]2[C:20]3[C:15](=[CH:16][C:17]([O:23][CH3:24])=[C:18]([CH2:21][OH:22])[CH:19]=3)[N:14]=[CH:13][N:12]=2)[CH:7]=[CH:8][CH:9]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 115734924-[(3-Chloro-2-fluorophenyl)amino]-7-methoxyquinazoline-6-carbaldehyde

Product 1

HCID 57979865{4-[(3-Chloro-2-fluorophenyl)amino]-7-methoxyquinazolin-6-yl}methanolYield 100%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Sodium borohydride (0.046 g, 1.21 mmol) was added to a stirred suspension of 4-[(3-chloro-2-fluorophenyl)amino]-7-methoxyquinazoline-6-carbaldehyde (0.20 g, 0.604 mmol) in methanol (1 ml) at 0° C., over period of 5 minutes. The reaction mixture was allowed to stir at room temperature for 10 minutes and concentrated to dryness. The resulting grey solid was washed with water (2×1 ml) and dried to a constant weight under high vacuum at 40° C. to afford {4-[(3-chloro-2-fluorophenyl)amino]-7-methoxyquinazolin-6-yl}methanol (0.2 g, 100%) as a grey solid; Mass Spectrum: (M+H)+ 334.

Workup

  1. concentrationconcentrated to dryness
  2. washThe resulting grey solid was washed with water (2×1 ml)
  3. customdried to a constant weight under high vacuum at 40° C.

Sources & evidence

ORD record
ord-6568c008c0534ba5829e75d4e95908cc
Source dataset
uspto-grants-2009_12
Patent number
US07632840B2

Reaction notes

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