Tetrahydrofuran → 3-Fluoro-5-(((1-methyl-5-oxo-1,2,3,5-tetrahydroimidazo[1,2-c]pyrimidin-7-yl)oxy)methyl)benzonitrile

온도

20 °C

To a solution of 3-cyano-5-fluorobenzoic acid (1.00 g, 6.06 mmol) in tetrahydrofuran (THF) (20 mL) was added di(1H-imidazol-1-yl)methanone (1.08 g, 6.66 mmol). The reaction mixture was stirred at 20° C. for 1 h. Then a suspension of NaBH4 (0.687 g, 18.2 mmol) in water (5 mL) was added dropwise. The reaction mixture was stirred at 20° C. for 20 h, quenched with saturated aqueous NH4Cl and extracted with ethyl acetate (20 mL×3). Combined organic portions were washed with saturated aqueous NaHCO3 (20 mL), brine (20 mL), dried over Na2SO4 and concentrated in vacuo to get the desired product as a white solid. 1HNMR (400 MHz, CDCl3): δ 4.697 (m, 2H) & 7.104˜7.400 (m, 3H).

1. additionwas added dropwise
2. stirringThe reaction mixture was stirred at 20° C. for 20 h
3. customquenched with saturated aqueous NH4Cl
4. extractionextracted with ethyl acetate (20 mL×3)
5. washCombined organic portions were washed with saturated aqueous NaHCO3 (20 mL), brine (20 mL)
6. dry with materialdried over Na2SO4
7. concentrationconcentrated in vacuo

ORD 기록

ord-03d4d8be6b6a42fc83b01c54f323f314

출처 데이터셋

uspto-grants-2015_03

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US08975400B2