Water → 4-bromo-N-(7-morpholinopyrazolo[1,5-a]pyrimidin-5-yl)benzamide

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Reaction Steps

7-Morpholinopyrazolo[1,5-a]pyrimidin-5-amine (9A, 1.0 g, 4.6 mmol) was suspended in pyridine (10 ml), and 4-bromobenzoyl chloride (1.1 g, 4.8 mmol) was then added at 0° C. After 1 hour, water (200 ml) was added and the resulting precipitate was collected on a fritted glass funnel, washed with water twice, and then dried under a stream of nitrogen for 3 hours to give analytically pure product 4-bromo-N-(7-morpholinopyrazolo[1,5-a]pyrimidin-5-yl)benzamide (9B, 1.6 g, 87%). 1H NMR (400 MHz, DMSO-d6) δ=11.13 (s, 1 H), 8.10 (d, J=2.3 Hz, 1 H), 8.01-7.93 (m, 2 H), 7.77-7.71 (m, 2 H), 7.37 (s, 1 H), 6.38 (d, J=2.3 Hz, 1 H), 3.88-3.81 (m, 4 H), 3.77-3.70 (m, 4 H); ESI-MS: m/z 402.2 (M+H)+.

Provenance & Evidence