Diisopropylethylamine → Methyl 5-phenyl-4-[4-(2-pyrrolidin-1-ylethoxymethyl)-1-piperidyl]thieno[2,3-d]pyrimidine-6-carboxylate

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To a stirred solution of methyl 4-chloro-5-phenyl-thieno[2,3-d]pyrimidine-6-carboxylate (0.850 g, 2.80 mmol) in THF (50 mL), was added diisopropylethylamine (0.73 mL, 4.20 mmol) and 4-(2-pyrrolidin-1-ylethoxymethyl)piperidine (0.890 g, 4.20 mmol) in one portion, and the reaction left to stir at room temperature for 2 hours. The reaction was diluted with water (50 mL) and extracted with ethyl acetate (3×50 mL). The reaction was dried over sodium sulphate, filtered and concentrated under reduced pressure. The crude material was purified by column chromatography using DCM: MeOH (0-25%) as eluent to afford the named product (1.012 g, 75%). m/z [M+H]+481; RT=3.03 min.

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