Triethylamine → 5-Chloro-N4-(1-(6-(3,3-difluoroazetidin-1-yl)-1-methyl-1H-pyrrolo[3,2-b]pyridin-5-yl)ethyl)pyrimidine-2,4,6-triamine

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Reaction Conditions

Reaction Steps

To a 10 mL vial were added 1-(6-(3,3-difluoroazetidin-1-yl)-1-methyl-1H-pyrrolo[3,2-b]pyridin-5-yl)ethanamine (61 mg, 0.23 mmol), 5,6-dichloropyrimidine-2,4-diamine (41.0 mg, 0.229 mmol) and Et3N (0.064 mL, 0.46 mmol) in DMF (2 mL). The resulting yellow solution was heated to 90° C. and stirred for 48 hours. The crude product was purified by preparative HPLC eluting with 30-55% ACN in water (with ammonium bicarbonate). The fractions containing the desired product were combined and lyophilized to give the title compound as a pale yellow solid (5 mg, 5%). 1H NMR (400 MHz, DMSO-d6) δ ppm 1.29-1.41 (m, 3 H), 3.73-3.86 (m, 3 H), 4.17-4.35 (m, 2 H), 4.43-4.58 (m, 2 H), 5.33-5.48 (m, 1 H), 5.69-5.80 (m, 2 H), 5.89-6.01 (m, 2 H), 6.32-6.43 (m, 1 H), 6.45-6.54 (m, 1 H), 7.37-7.43 (m, 1 H), 7.45-7.51 (m, 1 H); ESI-MS m/z [M+H]+ calc'd for C17H19ClF2N8, 409; found 409.

Provenance & Evidence