Diisopropylethylamine → 7-(2-Fluoro-4-methylsulfanyl-phenylamino)-pyrrolo[1,2-c]pyrimidine-6-carboxylic acid methyl ester

온도

0 °C

To a solution of N-(2-fluoro-4-methylsulfanyl-phenyl)-2-pyrimidin-4-ylmethyl-malonamic acid methyl ester (2 g, 5.72 mmol) and diisopropylethyl amine (2.9 mL, 17.2 mmol) in dioxane (30 mL) was added phosphorous (V) oxychloride (2.7 mL, 28.6 mmol) and the reaction mixture heated at reflux for 1 hour. The reaction mixture was cooled to 0° C. and quenched with water (10 mL). The reaction mixture was diluted with saturated aqueous sodium bicarbonate solution (20 mL) and extracted with ethyl acetate (3×10 mL). The combined organic fractions were washed with brine, dried (MgSO4) and concentrated in vacuo. The resultant residue was subjected to flash chromatography (SiO2, gradient 10-20% ethylacetate in cyclohexane) to yield the title compound as a light brown solid (0.80 g, 42%). LCMS (Method B): RT=3.70 min, M+H+=332.

1. temperaturethe reaction mixture heated
2. temperatureat reflux for 1 hour
3. customquenched with water (10 mL)
4. additionThe reaction mixture was diluted with saturated aqueous sodium bicarbonate solution (20 mL)
5. extractionextracted with ethyl acetate (3×10 mL)
6. washThe combined organic fractions were washed with brine
7. dry with materialdried (MgSO4)
8. concentrationconcentrated in vacuo

ORD 기록

ord-045306fa0ec2457085b46f4e35388be4

출처 데이터셋

uspto-grants-2013_07

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US08486963B2