Sodium hydride → 4-Chloro-6-(2,6-difluoro-phenylamino)-2-methylsulfanyl-pyrimidine-5-carbonitrile

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Reaction Steps

2,6-di-Fluoroaniline (2.66 mL, 24 mmol), DMSO (12 mL) and NaH (0.912 g, 22.8 mmol) were combined at 23°. When the foaming ceased 4,6-Dichloro-2-methylsulfanyl-pyrimidine-5-carbonitrile [Santilli, et al., J. Heterocycl. Chem. 1971, 8, 445-453] (5.0 g, 22.82 mmol) was added in DMSO (12 mL). The reaction exothermed and the temperature was moderated with cold H2O bath, then stirred at 23° for 3 h. The reaction was diluted with EtOAc (300 mL) and washed with H2O (4×) and satd aq NaCl (1×). Dried (Na2SO4) and concentrated to afford 6.21 g (82%) of a tan foam. LC MS m/z=313 (MH+), Rt=2.37 min.

Provenance & Evidence