Chloroacetaldehyde → 7-chloro-5-(1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazol-4-yl)imidazo[1,2-c]pyrimidine

温度

95 °C

To a solution of 6-chloro-2-(1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazol-4-yl)pyrimidin-4-amine (2.750 g, 8.439 mmol) in 60 mL of 1:1 absolute ethanol: pH=7 phosphate buffer were added sodium acetate (1.385 g, 16.88 mmol) and 2-chloroacetaldehyde (1.905 mL, 14.77 mmol) and the reaction mixture was then fitted with a condenser and heated to 95° C. overnight. The reaction was not complete so sodium acetate (1.385 g, 16.88 mmol) and 2-chloroacetaldehyde (1.905 mL, 14.77 mmol) were added and the reaction mixture was heated to 95° C. for four hours. After this time the reaction was allowed to cool to ambient temperature and was then diluted with aqueous saturated sodium bicarbonate (50 mL) and extracted with ethyl acetate. The organic layers were combined, dried over MgSO4, filtered, and concentrated under reduced pressure. The resulting residue was purified by silica gel chromatography eluting with 30-45% ethyl acetate in hexanes (1 L) to afford the title compound (1.16 g, 3.315 mmol, 39.29% yield). MS (apci) m/z=350.1 (M+H).

1. customthe reaction mixture was then fitted with a condenser
2. additionwere added
3. temperaturethe reaction mixture was heated to 95° C. for four hours
4. temperatureto cool to ambient temperature
5. extractionextracted with ethyl acetate
6. dry with materialdried over MgSO4
7. filtrationfiltered
8. concentrationconcentrated under reduced pressure
9. customThe resulting residue was purified by silica gel chromatography
10. washeluting with 30-45% ethyl acetate in hexanes (1 L)

ORDレコード

ord-67d63515ab9b45899887d6269679104e

出典データセット

uspto-grants-2015_02

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US08962596B2