Potassium Carbonate → 5-Phenyl-3-(2,2,2-trifluoroethyl)thieno[2,3-d]pyrimidin-4(3H)-one

HRID 1750315Notes

Reaction equation

[C:1]1([C:7]2[C:15]3[C:14](=[O:16])[NH:13][CH:12]=[N:11][C:10]=3[S:9][CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[F:17][C:18]([F:22])([F:21])[CH2:19]I.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.O>[C:1]1([C:7]2[C:15]3[C:14](=[O:16])[N:13]([CH2:19][C:18]([F:22])([F:21])[F:17])[CH:12]=[N:11][C:10]=3[S:9][CH:8]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 5-phenylthieno[2,3-d]pyrimidin-4(3H)-one (20 g, 88 mmol), 1,1,1-trifluoro-2-iodoethane (36.8 g, 175 mmol) and potassium carbonate (26.6 g, 193 mmol) in DMF (100 ml) was heated at 70° C. for 0.5 h and at 100° C. for 2 h. A further portion of 1,1,1-trifluoro-2-iodoethane (36.8 g, 175 mmol) was added and the resulting mixture was heated at 100° C. for a further 16 h. The reaction mixture was cooled down and diluted with water (750 ml) and the precipitate was filtered to give the title compound as a light yellow solid (13 g, 48%). LCMS RT=1.30 min, M+H+=311.1.

Workup

temperaturethe resulting mixture was heated at 100° C. for a further 16 h
temperatureThe reaction mixture was cooled down
filtrationthe precipitate was filtered

Sources & evidence

ORD record: ord-223bbe59f7604cada15721da2dcd3eba
Source dataset: uspto-grants-2015_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09156853B2

Reaction notes

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