Thionyl Chloride → 7-[(2E)-4-Chlorobut-2-enoyl]-N-(3-chloro-4-fluorophenyl)-5,6,7,8-tetrahydropyrido[4',3':4,5]thieno[2,3-d]pyrimidin-4-amine

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(2E)-4-Bromobut-2-enoic acid (1.48 g, 7.17 mmol) was stirred in thionylchloride (10 mL, 137 mmol) for 4 h. The mixture was then concentrated in vacuo. Twice, toluene was added and again removed in vacuo. The residue was dissolved in dichloromethane (14 mL). This solution was added to a solution of N-(3-chloro-4-fluorophenyl)-5,6,7,8-tetrahydropyrido[4′,3′:4,5]thieno[2,3-d]-pyrimidin-4-amine from Example 12A (2.00 g, 5.97 mmol) and DIPEA (1.93 g, 14.9 mmol) in DMF (35 mL) at −10° C. The mixture was stirred for 1.5 h at −10° C. and subsequently for 15 h at rt. The mixture was then diluted with water. Ethyl acetate was added, and the precipitate was collected by suction filtration to yield 1.50 g of a solid, which was identified by LC/MS as a mixture of the bromo- and chloro-allylic compound. It was used in the next step without further purification or separation.

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