Sodium borohydride → 4-{5-(1-Hydroxyethyl)-6-methyl-2-thioxo-1-[3-(trifluoromethyl)phenyl]-1,2,3,4-tetrahydro-4-pyrimidinyl}benzonitrile

HRID 230283Notes

Reaction equation

HRID 230283 reaction equation
[C:1]([C:4]1[CH:5]([C:22]2[CH:29]=[CH:28][C:25]([C:26]#[N:27])=[CH:24][CH:23]=2)[NH:6][C:7](=[S:21])[N:8]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([C:17]([F:20])([F:19])[F:18])[CH:12]=2)[C:9]=1[CH3:10])(=[O:3])[CH3:2].[BH4-].[Na+]>CO>[OH:3][CH:1]([C:4]1[CH:5]([C:22]2[CH:23]=[CH:24][C:25]([C:26]#[N:27])=[CH:28][CH:29]=2)[NH:6][C:7](=[S:21])[N:8]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([C:17]([F:20])([F:18])[F:19])[CH:12]=2)[C:9]=1[CH3:10])[CH3:2]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 115968194-{5-Acetyl-6-methyl-2-thioxo-1-[3-(trifluoromethyl)phenyl]-1,2,3,4-tetrahydro-4-pyrimidinyl}benzonitrile

Product 1

HCID 103646454-{5-(1-Hydroxyethyl)-6-methyl-2-thioxo-1-[3-(trifluoromethyl)phenyl]-1,2,3,4-tetrahydro-4-pyrimidinyl}benzonitrile

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

4-{5-Acetyl-6-methyl-2-thioxo-1-[3-(trifluoromethyl)phenyl]-1,2,3,4-tetrahydro-4-pyrimidinyl}benzonitrile (Example 1; 100 mg, 0.24 mmol) is dissolved in 3 ml methanol, and sodium borohydride (10 mg, 0.26 mmol) is added. After stirring at room temperature for 1 h, the crude mixture is purified via preparative HPLC (RP18-column; eluent: acetonitrile-water, gradient 10:90 to 90:10) to give the product as a 1.6:1-mixture of the two diastereomers.

Workup

  1. customthe crude mixture is purified via preparative HPLC (RP18-column; eluent: acetonitrile-water, gradient 10:90 to 90:10)
  2. customto give the product as a 1.6

Sources & evidence

ORD record
ord-c65d557e9e2946f28365cb7adbde23ba
Source dataset
uspto-grants-2009_07
Patent number
US07566723B2

Reaction notes

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