Sodium borohydride → 2-((4-(Hydroxymethyl)-3-(trifluoromethyl)-1H-pyrazol-1-yl)methyl)-6-methyl-5-phenyl thieno[2,3-d]pyrimidin-4(3H)-one

HRID 1091694Notes

Reaction equation

HRID 1091694 reaction equation
[CH3:1][C:2]1[S:23][C:5]2[N:6]=[C:7]([CH2:11][N:12]3[CH:16]=[C:15]([CH:17]=[O:18])[C:14]([C:19]([F:22])([F:21])[F:20])=[N:13]3)[NH:8][C:9](=[O:10])[C:4]=2[C:3]=1[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.[BH4-].[Na+]>C(Cl)Cl.CO>[OH:18][CH2:17][C:15]1[C:14]([C:19]([F:20])([F:22])[F:21])=[N:13][N:12]([CH2:11][C:7]2[NH:8][C:9](=[O:10])[C:4]3[C:3]([C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=4)=[C:2]([CH3:1])[S:23][C:5]=3[N:6]=2)[CH:16]=1

Participants

5

Reactant 2

HCID 4311764Sodium borohydride2×HCID 866303981-((6-Methyl-4-oxo-5-phenyl-3,4-dihydrothieno[2,3-d]pyrimidin-2-yl)methyl)-3-(trifluoromethyl)-1H-pyrazole-4-carbaldehyde

Product 1

HCID 665916232-((4-(Hydroxymethyl)-3-(trifluoromethyl)-1H-pyrazol-1-yl)methyl)-6-methyl-5-phenyl thieno[2,3-d]pyrimidin-4(3H)-oneYield 10.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 1-((6-methyl-4-oxo-5-phenyl-3,4-dihydrothieno[2,3-d]pyrimidin-2-yl)methyl)-3-(trifluoromethyl)-1H-pyrazole-4-carbaldehyde (97 mg, 0.232 mmol) in DCM (2 mL) and MeOH (2 mL) was added sodium borohydride (26 mg, 0.696 mmol) and the mixture was stirred overnight. Sodium borohydride (53 mg, 1.39 mmol) was added and the mixture was stirred for a further 20 h. The reaction mixture was quenched with water and concentrated in vacuo. The residue was taken up in 1:1 DMSO:MeCN, filtered and purified by preparative LCMS to give the title product as a white solid (10 mg, 0.024 mmol, 10%).

Workup

  1. stirringthe mixture was stirred for a further 20 h
  2. customThe reaction mixture was quenched with water
  3. concentrationconcentrated in vacuo
  4. filtrationMeCN, filtered
  5. custompurified by preparative LCMS

Sources & evidence

ORD record
ord-ab603b70f8094f3980c67aef3faf229f
Source dataset
uspto-grants-2012_03
Patent number
US08129397B2

Reaction notes

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