Trifluoroacetic acid → (S)-4-(2-amino-4-chloro-7-((4-methoxy-3,5-dimethylpyridin-2-yl)methyl)-7H-pyrrolo[2,3-d]pyrimidin-5-yl)but-3-ynyl 2-aminopropanoate

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Reaction Steps

A solution of 4-[2-Amino-4-chloro-7-(4-methoxy-3,5-dimethyl-pyridin-2-ylmethyl)-7H-pyrrolo[2,3-d]pyrimidin-5-yl]-but-3-yn-1-ol (see example 2) (51.7 mg), N-Boc alanine (53.3 mg), DMAP (33.7 mg), and EDCI (54.9 mg) in anhyrous DMA (4 mL) was stirred at rt overnight. Work-up (EtOAc; H2O) gave the crude Boc-protected intermediate. A solution of this intermediate (40 mg) in DCM (1.0 mL) was treated with TFA (0.2 mL) at rt for 5 min, and evaporated. The material was dissolved in MeOH (1 ml) and water (10 mL), and washed with Et2O (10 mL). The organic layer was discarded. The aqueous layer was brought to pH >7 with sat. aq. NaHCO3 and back-extracted with DCM. The title compound was isolates as a solid. HPLC Rt=4.37 min.

Provenance & Evidence