Methanol → N-(3-Chloro-4-fluorophenyl)-7-[(2E)-3-(1-methylpiperidin-2-yl)prop-2-enoyl]-5,6,7,8-tetrahydropyrido[4',3':4,5]thieno[2,3-d]pyrimidin-4-amine

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Reaction Conditions

Reaction Steps

In a separate flask, diethyl (2-{4-[(3-chloro-4-fluorophenyl)amino]-5,8-dihydropyrido[4′,3′:4,5]thieno[2,3-d]pyrimidin-7(6H)-yl}-2-oxoethyl)phosphonate from Example 13A (400 mg, 0.78 mmol) was dissolved in THF (1.0 mL). The solution was cooled to −78° C., and sodium hydride (60% in mineral oil, 31 mg, 0.78 mmol) was added. The mixture was stirred for 15 min, then solution A was added slowly. The mixture was slowly warmed to rt and stirred overnight. Methanol was added, and the solvents were removed in vacuo. The residue was purified by preparative HPLC to yield 90 mg (24%) of the title compound.

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