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

HRID 1091689Notes

Reaction equation

HRID 1091689 reaction equation
[F:1][C:2]([F:12])([F:11])[C:3]1[C:7]([CH2:8][CH2:9][OH:10])=[CH:6][NH:5][N:4]=1.Cl[CH2:14][C:15]1[NH:16][C:17](=[O:25])[C:18]2[CH:23]=[C:22]([CH3:24])[S:21][C:19]=2[N:20]=1.CC(C)([O-])C.[K+]>C1COCC1>[OH:10][CH2:9][CH2:8][C:7]1[C:3]([C:2]([F:1])([F:11])[F:12])=[N:4][N:5]([CH2:14][C:15]2[NH:16][C:17](=[O:25])[C:18]3[CH:23]=[C:22]([CH3:24])[S:21][C:19]=3[N:20]=2)[CH:6]=1

Participants

5

Reactant 3

HCID 64916832-(Chloromethyl)-6-methylthieno[2,3-d]pyrimidin-4(3H)-oneHCID 23665647Potassium tert-butoxideHCID 178520360HCID 178520360, compound

Product 1

HCID 665916802-((4-(2-Hydroxyethyl)-3-(trifluoromethyl)-1H-pyrazol-1-yl)methyl)-6-methylthieno[2,3-d]pyrimidin-4(3H)-oneYield 32%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
75 °C

Procedure

A mixture of 2-(3-(trifluoromethyl)-1H-pyrazol-4-yl)ethanol (50 mg, 0.278 mmol), 2-(chloromethyl)-6-methylthieno[2,3-d]pyrimidin-4(3H)-one (60 mg, 0.278 mmol) and potassium tert-butoxide (62 mg, 0.07 mL, 0.555 mmol) in THF (3 mL) was heated to 75° C. for 4 h. The reaction mixture was allowed to cool to RT before being filtered and concentrated in vacuo. The residue was purified by preparative reverse phase HPLC to give the title compound as a white solid (32 mg, 0.089 mmol, 32%).

Workup

  1. temperatureto cool to RT
  2. filtrationbefore being filtered
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by preparative reverse phase HPLC

Sources & evidence

ORD record
ord-1fb475d67c064d5d8d0f5da3a8a4b26c
Source dataset
uspto-grants-2012_03
Patent number
US08129397B2

Reaction notes

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