[H-].[Na+].[C:3]1([CH2:9][C:10]#[N:11])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.Cl[C:13]1[C:14]2[S:25][CH:24]=[CH:23][C:15]=2[N:16]=[C:17]([C:19]([F:22])([F:21])[F:20])[N:18]=1.O>CN(C=O)C.C1(C)C=CC=CC=1>[C:3]1([CH:9]([C:13]2[C:14]3[S:25][CH:24]=[CH:23][C:15]=3[N:16]=[C:17]([C:19]([F:21])([F:22])[F:20])[N:18]=2)[C:10]#[N:11])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1A suspension of NaH (60% dispersion in oil, 60 mg, 1.5 mmol) in DMF (5 mL) and toluene (15 mL) at room temperature was treated with phenylacetonitrile (0.16 g, 1.37 mmol), stirred for 10 min, treated with a solution of 4-chloro-2-trifluoromethylthieno[3,2-d]pyrimidine (0.3 g, 126 mmol) in DMF (2 mL), stirred for 15 min, treated with water (5 mL) and the phases separated. The aqueous phase was extracted with EtOAc (2×50 mL), the combined organic phase washed with water (3×10 mL), brine (10 mL), dried (MgSO4), concentrated in vacuo and the resulting orange oily solid crystallised from heptane to give the title compound (0.1 g, 25%) as a gold solid.
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