Sodium hydride → (4-ethyl-1,3-thiazol-2(3H)-ylidene)(2-{[4-(morpholin-4-ylmethyl)benzyl]oxy}pyrimidin-4-yl)acetonitrile

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Reaction Steps

To a suspension of NaH (99 mg, 2.27 mmol) in ACN (4 mL) was added a solution of N-(4-hydroxymethylbenzyl)morpholine 313 mg, 1.51 mmol) in ACN (4 mL). The mixture was stirred 1 h at rt. Then (2-chloropyrimidin-4-yl)(4-ethyl-1,3-thiazol-2(3H)-ylidene)acetonitrile (200 mg, 0.76 mmol) was added portion wise. The resulting mixture was heated up at 80° C. for 5 h. After cooling down to rt the ACN was evaporated. EtOAc (5 mL) was added to the residue. After one night at 4° C., the yellow solid was filtered off affording the title compound as a free base (HPLC (max plot) 73.9%). The solid was taken up in DCM and excess TFA then ether were added. The precipitate formed was filtered off, washed with ether (3×) then dried under reduced pressure at 40° C. overnight, affording 409 mg of the title compound as a diTFA salt (Yellow powder, Y=81.1%)

Provenance & Evidence