Sodium borohydride → 1-{4-[(3-Chloro-2-fluorophenyl)amino]-7-methoxyquinazolin-6-yl}ethanol

HRID 1867760Notes

Reaction equation

HRID 1867760 reaction equation
[Cl:1][C:2]1[C:3]([F:24])=[C:4]([NH:8][C:9]2[C:18]3[C:13](=[CH:14][C:15]([O:22][CH3:23])=[C:16]([C:19](=[O:21])[CH3:20])[CH:17]=3)[N:12]=[CH:11][N:10]=2)[CH:5]=[CH:6][CH:7]=1.[BH4-].[Na+]>>[Cl:1][C:2]1[C:3]([F:24])=[C:4]([NH:8][C:9]2[C:18]3[C:13](=[CH:14][C:15]([O:22][CH3:23])=[C:16]([CH:19]([OH:21])[CH3:20])[CH:17]=3)[N:12]=[CH:11][N:10]=2)[CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 4311764Sodium borohydrideHCID 579798001-{4-[(3-Chloro-2-fluorophenyl)amino]-7-methoxyquinazolin-6-yl}ethanone

Product 1

HCID 579798031-{4-[(3-Chloro-2-fluorophenyl)amino]-7-methoxyquinazolin-6-yl}ethanol

Procedure

1-{4-[(3-Chloro-2-fluorophenyl)amino]-7-methoxyquinazolin-6-yl}ethanone was reduced with sodium borohydride using an analogous procedure to that described for the equivalent step in Example 62 to give 1-{4-[(3-chloro-2-fluorophenyl)amino]-7-methoxyquinazolin-6-yl}ethanol; 1H NMR Spectrum: (DMSO d6) 1.38 (d, 3H); 3.95 (s, 3H); 5.12 (m, 1H); 5.28 (d, 1H); 7.16 (s, 1H); 7.24 (t, 1H); 7.45 (m, 2H); 8.39 (s, 1H); 8.48 (s, 1H); 9.93 (s, 1H). Mass Spectrum: (M+H)+ 348.

Sources & evidence

ORD record
ord-ba410f711a5247e8be4cb02840cbb993
Source dataset
uspto-grants-2009_12
Patent number
US07632840B2

Reaction notes

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