Diisopropylethylamine → HCID 86699873, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 2-tert-butyl-5-((2-((tert-butyldimethylsilyloxy)methyl)-3-(1-methyl-6-oxo-5-(pyrimidin-4-ylamino)-1,6-dihydropyridin-3-yl)phenylamino)-methyl)thiazole-4-carboxylic acid (125e) (500 mg, 0.78 mmol) in methylene chloride (40 mL) was added N,N-Diisopropylethylamine (503 mg, 3.9 mmol) and N,N,N′,N′-tetramethyl-O-(7-azabenzotriazol-1-yl)uronium hexafluorophosphate (900 mg, 2.37 mmol). The mixture was stirred at 25° C. for 2 h. After flash column purification with PE:EA (1:3 to 1:6) as eluent, 125 was obtained as white solid (32 mg, 10%). LCMS: (M+H)+ 503. 1H NMR (500 MHz, MeOD) ppm 8.84 (d, J=2 Hz, 1H), 8.66 (s, 1 H), 8.29 (d, J=5.5 Hz, 1H), 7.49-7.56 (m, 4 H), 7.09 (d, J=5.5 Hz, 2 H), 5.04 (s, 2 H), 4.57 (s, 2 H), 3.73 (s, 3 H), 1.54 (s, 9 H).

Provenance & Evidence