Chlorodifluoromethane → HCID 18971791, compound

Temperature

60 °C

Chlorodifluoromethane was bubbled into a solution of (102 mg, 0.459 mmol, 1.0 eq) of tetrahydro-5-(4-methoxy-3-hydroxyphenyl)-2(1H)-pyrimidinone and 64 mg (1.61 mmol, 3.5 eq) of NaOH in 3 ml of H2O and 3 ml of 1,4-dioxane. After 1 hour at room temperature, the reaction mixture was heated to 60° C. for 1.5 hours. Chlorodifluoromethane was bubbled in continuously. The reaction mixture was cooled to room temperature, poured into 150 ml of H2O and 75 ml of ethyl acetate, extracted twice with ethyl acetate. The ethyl acetate extracts were washed twice with 2N NaOH, once with brine, dried over Na2SO4, and concentrated to yield 13.5 mg of a white solid, which was recrystallized from ethyl acetate-hexane to afford 8.4 mg, 7%, of off-white crystals. M.P.: 215°-216° C. Elemental Analysis: Calc'd for C12 H14N2O3F2 : Calc'd: C, 52.95; H, 5.18; N, 10.29. Found: C, 52.88; H, 4.91; N, 10.13.

1. customChlorodifluoromethane was bubbled in continuously
2. temperatureThe reaction mixture was cooled to room temperature
3. additionpoured into 150 ml of H2O and 75 ml of ethyl acetate
4. extractionextracted twice with ethyl acetate
5. washThe ethyl acetate extracts were washed twice with 2N NaOH, once with brine
6. dry with materialdried over Na2SO4
7. concentrationconcentrated

ORD record

ord-1b7d9e97c8564a66aedb2cfe83e304c2

Source dataset

uspto-grants-1998_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05814651