Phosphorus oxychloride → 4,5-dichloro-N-(1-methyl-1H-pyrazol-4-yl)-7H-pyrrolo[2,3-d]pyrimidin-2-amine

Participants

Reaction Conditions

Reaction Steps

5-chloro-N-(1-methyl-1H-pyrazol-4-yl)-4-(1-phenylethoxy)-7H-pyrrolo[2,3-d]pyrimidin-2-amine (1.65 g, 4.47 mmol) was suspended in POCl3 (9 mL) and the reaction was heated to 70° C. for 40 min, then further heated to 100° C. for 0.5 hr. The reaction mixture was cooled, concentrated in vacuo and diluted with water (50 mL). NH4OH was added to adjusted the pH 8 and the mixture was extracted with EtOAc (three×75 mL), and concentrated under reduced pressure. A precipitate was formed upon concentrating that was filtered off, and the filtrate was concentrated and the resulting residue was purified by flash chromatography eluting with a gradient of 30% 100% EtOAc in heptanes to afford the title compound (282 mg, 22% yield). 1H NMR (400 MHz, DMSO-d6) δ ppm 11.96 (br. s., 1H) 9.58 (br. s., 1H) 7.87 (s, 1H) 7.52 (s, 1H) 7.37 (s, 1H) 3.81 (s, 3H). m/z (APCI+) for C10H8Cl2N6 283.15 (M+H)+.

Provenance & Evidence