Potassium Hydroxide → Ethyl 1-[5-[2-(ethylcarbamoylamino)-7-ethynyl-1,3-benzothiazol-5-yl]pyrimidin-2-yl]-4-methyl-piperidine-4-carboxylate

Participants

Reaction Steps

To an ice-cold solution of ethyl 1-[5-[2-(ethylcarbamoylamino)-7-(2-trimethylsilylethynyl)-1,3-benzothiazol-5-yl]pyrimidin-2-yl]-4-methyl-piperidine-4-carboxylate (1.1 g, 1.94 mmol) in EtOH (40 mL) was added powdered KOH (0.24 g, 4.21 mmol) and the mixture stirred at rt for 4 h. After completion of reaction (by TLC), the solvent was evaporated under reduced pressure, water added and extracted with EtOAc (3×100 mL). The combined organic layer was washed with brine and water then dried over anhydrous Na2SO4. Solvent was evaporated under reduced pressure to obtain the product as a pale yellow solid (0.8 g, 83% yield). 1H NMR (DMSO-d6): δ 1.11 (t, J=7.20 Hz, 3H), 1.21 (m, 6H), 1.42 (m, 2H), 2.04 (m, 2H), 3.20 (m, 2H), 3.33 (q, J=7.20, 2H), 4.13 (q, J=6.80 Hz, 2H), 4.25 (m, 2H), 4.67 (s, 1H), 6.80 (br s, 1H), 7.61 (s, 1H), 7.94 (s, 1H); 8.78 (s, 2H) and 10.86 (br s, 1H). MS: 493.12 [M+H]+.

Provenance & Evidence