Butanethiol → 4-[5-(3-{[4-(Butylsulfanyl)pyrimidin-2-yl]amino}-5-methylphenyl)-1,3-thiazol-2-yl]-1,4-diazepan-2-one

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Reaction Steps

Sodium bis(trimethylsilyl)amide (164 μL, 1.0 M, 0.164 mmol) was added to a solution of 1-butanethiol (28.1 μL, 0.262 mmol) stirring in DMF (327 μL) at room temperature in an oven-dried vial. Stirred for 15 minutes, then added 4-[5-(3-methyl-5-{[4-(methylsulfonyl)-2-pyrimidinyl]amino}phenyl)-1,3-thiazol-2-yl]-1,4-diazepan-2-one (30 mg, 0.065 mmol). Stirred at room temperature for 30 minutes, diluted with ethyl acetate (10 mL), and washed with 1:1 water:brine (10 mL). The organic extracts were dried (Na2SO4), filtered, and concentrated in vacuo. Purified by CombiFlash (100:0 to 0:20 dichloromethane:methanol) to afford 4-[5-(3-{[4-(butylsulfanyl)pyrimidin-2-yl]amino}-5-methylphenyl)-1,3-thiazol-2-yl]-1,4-diazepan-2-one (14.6 mg, 0.031 mmol, 48% yield) as a white solid. MS APCI: [M+H]+ m/z 469.2. 1H NMR (500 MHz, DMSO) δ 9.52 (s, 1H), 8.13 (d, J=5.3 Hz, 1H), 7.60 (dd, J=4.9 Hz, 10.3 Hz, 2H), 7.45 (s, 1H), 7.43 (s, 1H), 6.92 (s, 1H), 6.72 (d, J=5.3 Hz, 1H), 4.16 (s, 2H), 3.84-3.73 (m, 2H), 3.25-3.12 (m, 4H), 2.26 (s, 3H), 1.78 (m, 2H), 1.59 (m, 2H), 1.35 (dd, J=7.4 Hz, 14.9 Hz, 2H), 0.83 (t, J=7.4 Hz, 3H).

Provenance & Evidence