Potassium Phosphate, Tribasic → HCID 75204434, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of (S)-5-bromo-N-(1-(pyrrolo[1,2-a]pyrazin-1-yl)pyrrolidin-3-yl)pyrimidine-2-carboxamide (0.25 g, 0.65 mmol, 1 eq) in 2 mL of toluene was added 2-cyclopropyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (0.16 g, 1.86 mmol, 2.8 eq), followed by PCy3 (0.033 g, 0.11 mmol, 0.2 eq), K3PO4 (0.48 g, 2.3 mmol, 3.5 eq) in 0.1 mL of H2O and Pd(OAc)2 (0.013 g, 0.06 mmol, 0.1 eq). After heating for 1 h at 120° C. the mixture was filtered and purified by HPLC to afford (S)-5-cyclopropyl-N-(1-(pyrrolo[1,2-a]pyrazin-1-yl)pyrrolidin-3-yl)pyrimidine-2-carboxamide (0.009 g, 0.026 mmol, 4%). 1H NMR (400 MHz, CD3OD) δ 8.64 (s, 2 H), 7.76 (m, 1 H), 7.71 (d, J=5.4 Hz, 1 H), 7.54 (s, 1 H), 6.92 (dd, J=2.6, 4.4 Hz, 1 H), 6.84 (d, J=5.5 Hz, 1 H), 5.00-3.60 (br, 5 H), 2.65-2.30 (br, 2 H), 2.07-2.02 (m, 1 H), 1.23-1.18 (m, 2 H), 0.96-0.91 (m, 2 H); MS: (ES) m/z calculated for C19H20N6O [M+H]+ 349.2, found 349.

Provenance & Evidence