2-(chloromethyl)-6-methyl-5-phenyl-3H,4H-thieno(2,3-d)pyrimidin-4-one → 1-((6-Methyl-4-oxo-5-phenyl-3,4-dihydrothieno[2,3-d]pyrimidin-2-yl)methyl)-3-(trifluoromethyl)-1H-pyrazole-4-carbaldehyde

HRID 1091693Notes

Reaction equation

HRID 1091693 reaction equation
[F:1][C:2]([F:11])([F:10])[C:3]1[C:7]([CH:8]=[O:9])=[CH:6][NH:5][N:4]=1.CC(C)([O-])C.[K+].Cl[CH2:19][C:20]1[NH:21][C:22](=[O:36])[C:23]2[C:28]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)=[C:27]([CH3:35])[S:26][C:24]=2[N:25]=1>C1COCC1>[CH3:35][C:27]1[S:26][C:24]2[N:25]=[C:20]([CH2:19][N:5]3[CH:6]=[C:7]([CH:8]=[O:9])[C:3]([C:2]([F:1])([F:10])[F:11])=[N:4]3)[NH:21][C:22](=[O:36])[C:23]=2[C:28]=1[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1

Participants

5

Reactant 3

HCID 23930692-(chloromethyl)-6-methyl-5-phenyl-3H,4H-thieno(2,3-d)pyrimidin-4-oneHCID 23665647Potassium tert-butoxideHCID 178519884HCID 178519884, compound

Product 1

HCID 866303981-((6-Methyl-4-oxo-5-phenyl-3,4-dihydrothieno[2,3-d]pyrimidin-2-yl)methyl)-3-(trifluoromethyl)-1H-pyrazole-4-carbaldehydeYield 38.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred suspension of 3-(trifluoromethyl)-1H-pyrazole-4-carbaldehyde (100 mg, 0.609 mmol) and potassium tert-butoxide (137 mg, 1.22 mmol) in THF (3 mL) was added 2-(chloromethyl)-6-methyl-5-phenylthieno[2,3-d]pyrimidin-4(3H)-one (177 mg, 0.609 mmol) and the resultant solution was stirred at RT for 2 days. The reaction mixture was quenched with water and concentrated in vacuo to give the crude product as a beige solid (97 mg, 0.232 mmol, 38%). The material was used without further purification.

Workup

  1. customThe reaction mixture was quenched with water
  2. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-123a114657704bcfae729ff0f0561ac8
Source dataset
uspto-grants-2012_03
Patent number
US08129397B2

Reaction notes

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