反应 #92311

反应方程式

dimethylamine

(R)-5-(2-(2,5-difluorophenyl)pyrrolidin-1-yl)pyrazolo[1,5-a]pyrimidin-3-amine

methyl 2-chloro-2-oxoacetate

DIEA

→

final product

收率 73.0%

(R)—N1-(5-(2-(2,5-difluorophenyl)pyrrolidin-1-yl)pyrazolo[1,5-a]pyrimidin-3-yl)-N2,N2-dimethyloxalamide

收率 73.0%

溶剂

DCM

反应条件

后处理

1. 1
   温度The reaction was heated
2. 2
   温度to gentle reflux for a few minutes
3. 3
   温度to cool back to ambient temperature
4. 4
   浓缩The reaction was concentrated
5. 5
   其他directly purified by reverse phase column chromatography
6. 6
   洗涤eluting with 5 to 60% acetonitrile/water

实验过程

To a DCM (1 mL) solution of (R)-5-(2-(2,5-difluorophenyl)pyrrolidin-1-yl)pyrazolo[1,5-a]pyrimidin-3-amine (Preparation B; 50 mg, 0.16 mmol) was drop-wise added methyl 2-chloro-2-oxoacetate (19.4 mg, 0.159 mmol), followed by DIEA (0.0829 mL, 0.476 mmol). After the mild exothermal subsided and the reaction cooled back to ambient temperature, dimethylamine (0.8 mL, 1.6 mmol) [2M, THF] was added. The reaction was heated to gentle reflux for a few minutes, allowed to cool back to ambient temperature and stirred for 1 hour to reach completion. The reaction was concentrated and directly purified by reverse phase column chromatography, eluting with 5 to 60% acetonitrile/water to yield the final product as a pale-yellowish solid (48 mg, 73% yield). MS (apci) m/z=415.1 (M+H).

来源