Sodium borohydride → (4-Amino-6-{4-[4-(4-fluoro-3-trifluoromethyl-phenyl)-1-methyl-1H-imidazol-2-yl]-piperidin-1-yl}-pyrimidin-5-yl)-methanol

HRID 2283981Notes

Reaction equation

HRID 2283981 reaction equation
[NH2:1][C:2]1[C:7]([CH:8]=[O:9])=[C:6]([N:10]2[CH2:15][CH2:14][CH:13]([C:16]3[N:17]([CH3:32])[CH:18]=[C:19]([C:21]4[CH:26]=[CH:25][C:24]([F:27])=[C:23]([C:28]([F:31])([F:30])[F:29])[CH:22]=4)[N:20]=3)[CH2:12][CH2:11]2)[N:5]=[CH:4][N:3]=1.[BH4-].[Na+]>CCO>[NH2:1][C:2]1[C:7]([CH2:8][OH:9])=[C:6]([N:10]2[CH2:15][CH2:14][CH:13]([C:16]3[N:17]([CH3:32])[CH:18]=[C:19]([C:21]4[CH:26]=[CH:25][C:24]([F:27])=[C:23]([C:28]([F:31])([F:30])[F:29])[CH:22]=4)[N:20]=3)[CH2:12][CH2:11]2)[N:5]=[CH:4][N:3]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 894427184-amino-6-(4-{4-[4-fluoro-3-(trifluoromethyl)phenyl]-1-methyl-1H-imidazol-2-yl}piperidin-1-yl)pyrimidine-5-carbaldehyde

Product 1

HCID 89445412(4-Amino-6-{4-[4-(4-fluoro-3-trifluoromethyl-phenyl)-1-methyl-1H-imidazol-2-yl]-piperidin-1-yl}-pyrimidin-5-yl)-methanolYield 65%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The reaction mixture of 4-amino-6-(4-{4-[4-fluoro-3-(trifluoromethyl)phenyl]-1-methyl-1H-imidazol-2-yl}piperidin-1-yl)pyrimidine-5-carbaldehyde (23.00 mg; 0.05 mmol; 1.0 eq.) and sodium borohydride (7.8 mg; 0.21 mmol; 4.0 eq.) in EtOH (2.00 ml) was stirred at room temperature over weekend. The reaction mixture was workup and purified by reverse phase chromatography (Yamazen, acetonitrile/0.1% NH4OH in water). The pure fractions were lyophilized to afford the title compound in 65% yield. LC-MS: (M+1=451, obsd.=451).

Workup

  1. custompurified by reverse phase chromatography (Yamazen, acetonitrile/0.1% NH4OH in water)

Sources & evidence

ORD record
ord-d585f9fe3ccd4821b5186c7a5e1a756d
Source dataset
uspto-grants-2015_09
Patent number
US09145392B2

Reaction notes

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