HCID 2166334, compound → HCID 21265538, compound

Temperature

5 °C

Ethyl 3-amino-4,4,4-trifluoro-2-methylcrotonate (26.0 g) was dissolved in DMF (123 ml). To this solution, a suspension of sodium methoxide in DNF (7.78 g) was added dropwise at 0° C., and the mixture was stirred at 5° C. for 30 minutes. Then, a DMF solution of ethyl N-(4-bromo-2-fluoro-phenyl)carbamate (31.44 g) was added dropwise thereto, and the mixture was stirred at 130° C. for 5 hours. After the reaction, DMF was distilled off under reduced pressure, and the residue was acidified by adding diluted hydrochloric acid thereto. This was extracted with ethyl acetate, washed with water, and then dried over anhydrous magnesium sulfate. Ethyl acetate was distilled off, and the resulting residue was crystallized from ethyl acetate-n-hexane (1:3 v/v) to obtain the objective 3-(4-bromo-2-fluorophenyl)-5-methyl-6-trifluoromethyl-2,4(1H,3H)-pyrimidinedione (18.78 g).

1. additionwas added dropwise at 0° C.
2. stirringthe mixture was stirred at 130° C. for 5 hours
3. distillationwas distilled off under reduced pressure
4. additionby adding diluted hydrochloric acid
5. extractionThis was extracted with ethyl acetate
6. washwashed with water
7. dry with materialdried over anhydrous magnesium sulfate
8. distillationEthyl acetate was distilled off
9. customthe resulting residue was crystallized from ethyl acetate-n-hexane (1:3 v/v)

ORD record

ord-97229743c1c04a3ca01a9325971d6085

Source dataset

uspto-grants-2001_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06174839B1