Hydrochloric Acid → Methyl 5-fluoropyrimidine-2-carboxylate

온도

80 °C

To a solution of 5-fluoropyrimidine-2-carbonitrile (513 mg, 4.17 mmol) in MeOH (5 mL) was added 5 mL of concentrated HCl. The mixture was stirred at 80° C. for 2 h. The solution was allowed to cool to room temperature and then treated with a small amount of saturated aqueous NaHCO3 solution and a larger amount of solid NaHCO3. The solution was used to keep everything homogeneous. When the pH reached 6-7 the aqueous layer was extracted with 10% EtOAc/DCM. The combined organic layers containing the ester were dried over Na2SO4. The aqueous layer was acidified to pH 3-4 with 1N HCl and then extracted with 10% EtOAc/DCM to afford the acid. The ester layer was filtered, concentrated in vacuo to a white solid (460 mg, 71%). MS (ESI): mass calcd. C6H5FN2O2, 156.03; m/z found, 157.1 [M+H]+. 1H NMR (500 MHz, CDCl3): 8.80 (s, 2H), 4.07 (s, 3H).

1. temperatureto cool to room temperature
2. extractionwas extracted with 10% EtOAc/DCM
3. additionThe combined organic layers containing the ester
4. dry with materialwere dried over Na2SO4
5. extractionextracted with 10% EtOAc/DCM
6. customto afford the acid
7. filtrationThe ester layer was filtered
8. concentrationconcentrated in vacuo to a white solid (460 mg, 71%)

ORD 기록

ord-d69c51352dd24e1fb8a59a28cfbf0887

출처 데이터셋

uspto-grants-2015_08

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US09102686B2