Methanol → 2-((4-(Hydroxymethyl)-3-(trifluoromethyl)-1H-pyrazol-1-yl)methyl)-6-methylthieno[2,3-d]pyrimidin-4(3H)-one

HRID 1091691Notes

Reaction equation

HRID 1091691 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[CH:3]=1.CO.[BH4-].[Na+]>C(Cl)Cl>[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[CH:3]=[C:2]([CH3:1])[S:23][C:5]=3[N:6]=2)[CH:16]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 4311764Sodium borohydrideHCID 866303971-((6-Methyl-4-oxo-3,4-dihydrothieno[2,3-d]pyrimidin-2-yl)methyl)-3-(trifluoromethyl)-1H-pyrazole-4-carbaldehyde

Product 1

HCID 665915302-((4-(Hydroxymethyl)-3-(trifluoromethyl)-1H-pyrazol-1-yl)methyl)-6-methylthieno[2,3-d]pyrimidin-4(3H)-oneYield 28%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1-((6-Methyl-4-oxo-3,4-dihydrothieno[2,3-d]pyrimidin-2-yl)methyl)-3-(trifluoromethyl)-1H-pyrazole-4-carbaldehyde (100 mg, 0.292 mmol) was dissolved in a 1:1 DCM:MeOH solution (2 mL) and sodium borohydride (33 mg, 0.876 mmol) added. After 30 min the mixture was quenched by addition of water (1 mL) then concentrated in vacuo. Purification by flash column chromatography-silica gel and elution with 3% MeOH:DCM resulted in a white solid which was recrystallised from isopropanol and freeze dried to give the title compound as a white solid (28 mg, 0.081 mmol, 28%).

Workup

  1. customAfter 30 min the mixture was quenched by addition of water (1 mL)
  2. concentrationthen concentrated in vacuo
  3. customPurification
  4. washby flash column chromatography-silica gel and elution with 3% MeOH
  5. customDCM resulted in a white solid which
  6. customwas recrystallised from isopropanol and freeze
  7. customdried

Sources & evidence

ORD record
ord-2358a72046234964bdf484dffe235f22
Source dataset
uspto-grants-2012_03
Patent number
US08129397B2

Reaction notes

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