Nitrogen → HCID 86719383, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 6-chloro-5-iodo-7-(3-nitrophenyl)-7H-pyrrolo[2,3-d]pyrimidin-4-amine (18) (1.4 g, 3.4 mmol), 4-chlorophenylboronic acid (696 mg, 4.5 mmol), Pd(dppf)Cl2.DCM (140 mg, 0.17 mmol) and Na2CO3 (1.1 g, 10.3 mmol) in DME (30 mL) and H2O (15 mL) was purged with N2 before heated to 90° C. overnight. After cooled down to r.t., the reaction was quenched with H2O (50 mL). The resulting mixture was extracted with DCM contained 25% i-PrOH(50 mL×3). The combined organic phase were washed with brine, dried over Na2SO4 and concentrated. The crude product was purified by column chromatographic (silica gel, 0 to 50% EA in a mixture of PE & DCM (1:1) and then 0 to 5% MeOH in DCM) to afford 6-chloro-5-(4-chlorophenyl)-7-(3-nitrophenyl)-7H-pyrrolo[2,3-d]pyrimidin-4-amine (19) (1.3 g, 91% yield) as a yellow solid. LC-MS (ESI): m/z (M/M+2) 399.9/401.9.

Provenance & Evidence