反应详情
EQUATION
反应方程式
REACTANTS
反应物
PRODUCTS
生成物
AUXILIARIES
试剂、催化剂与溶剂
CONDITIONS
反应条件
- 温度
- 0 °C
PROCEDURE
实验过程
Ethyl 1-[5-[7-(dimethoxymethyl)-2-(ethylcarbamoylamino)-1,3-benzothiazol-5-yl]pyrimidin-2-yl]-4-ethyl-piperidine-4-carboxylate (35 mg, 0.063 mmol) was dissolved in DCM (2 mL), cooled to 0° C. and treated sequentially with Et3SiH (50 μL, 0.313 mmol) and BF3:OEt2 (15 μL, 0.119 mmol) and the mixture stirred for 10 mins then allowed to warm to rt. After 40 mins additional Et3SiH (50 μL, 0.313 mmol) was added at rt followed by BF3:OEt2 (15 μL, 0.119 mmol) and the mixture stirred for 2.5 h after which time the reaction was diluted with sat. NaHCO3 (aq), extracted with DCM (3×), dried and the solvent evaporated to yield the crude product (31.7 mg). The crude product was purified on 12 g SiO2 using EtOAc/Cyclohexane gradient 0-0% 3CV, 0-100% 30CV, 100-100% 5CV to yield the desired compound (22.3 mg, 73%). 1H NMR (CDCl3) δ 8.59 (s, 2H), 7.79 (d, J=1.2 Hz, 1H), 7.25 (d, J=0.9 Hz, 1H), 4.66 (s, 2H), 4.53 (dt, J=13.7, 3.5 Hz, 2H), 4.22 (q, J=7.1 Hz, 2H), 3.51-3.40 (m, 2H), 3.38 (s, 3H), 3.22-3.07 (m, 2H), 2.23 (d, J=13.4 Hz, 2H), 1.59 (q, J=7.5 Hz, 2H), 1.48-1.43 (m, 2H), 1.29 (dd, J=10.0, 4.1 Hz, 6H), 0.85 (t, J=7.5 Hz, 3H). MS: 527.15 [M+H]+
WORKUP
后处理
- temperatureto warm to rt
- extractionextracted with DCM (3×)
- customdried
- customthe solvent evaporated
- customto yield the crude product (31.7 mg)
- customThe crude product was purified on 12 g SiO2