Ethyl 3-amino-4,4,4-trifluorocrotonate → 3-(4-Bromo-5-ethoxy-2-fluorophenyl)-6-trifluoromethyl-2,4(1H,3H)-pyrimidinedione

HRID 566183ノート

反応式

HRID 566183 の反応式
[NH2:1]/[C:2](/[C:9]([F:12])([F:11])[F:10])=[CH:3]\[C:4]([O:6]CC)=O.C[O-].[Na+].[Br:16][C:17]1[C:22]([O:23][CH2:24][CH3:25])=[CH:21][C:20]([NH:26][C:27](=O)[O:28]CC)=[C:19]([F:32])[CH:18]=1>CN(C=O)C>[Br:16][C:17]1[C:22]([O:23][CH2:24][CH3:25])=[CH:21][C:20]([N:26]2[C:4](=[O:6])[CH:3]=[C:2]([C:9]([F:10])([F:11])[F:12])[NH:1][C:27]2=[O:28])=[C:19]([F:32])[CH:18]=1

参加物

5

反応物 3

HCID 5702529Ethyl 3-amino-4,4,4-trifluorocrotonateHCID 10942334Sodium MethoxideHCID 21265588ethyl N-(4-bromo-5-ethoxy-2-fluorophenyl)carbamate

生成物 1

HCID 212655333-(4-Bromo-5-ethoxy-2-fluorophenyl)-6-trifluoromethyl-2,4(1H,3H)-pyrimidinedione

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒3 回

反応条件

温度
5 °C

実験手順

Ethyl 3-amino-4,4,4-trifluorocrotonate (3.42 g) was dissolved in DMF (19 ml). To this solution, a suspension of sodium methoxide (1.10 g) in DMF was added dropwise at 5° C., and the mixture was stirred at 5° C. for 30 minutes. Then, a DNF solution of ethyl N-(4-bromo-5-ethoxy-2-fluorophenyl)-carbamate was added dropwise thereto, and the mixture was stirred at 130° C. for 4 hours. After the reaction, DMF was distilled off under reduced pressure. Then, the residue was acidified by adding diluted hydrochloric acid thereto. This was extracted with ethyl acetate, washed with water, and dried over anhydrous magnesium sulfate. Then, ethyl acetate was distilled off, and the resulting residue was crystallized from a mixed solvent of ethyl acetate and n-hexane (1:3 v/v) to obtain the objective 3-(4-bromo-5-ethoxy-2-fluorophenyl)-6-trifluoromethyl-2,4(1H,3H)-pyrimidinedione (3.63 g).

後処理

  1. additionwas added dropwise at 5° C.
  2. stirringthe mixture was stirred at 130° C. for 4 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. distillationThen, ethyl acetate was distilled off
  9. customthe resulting residue was crystallized from a mixed solvent of ethyl acetate and n-hexane (1:3 v/v)

出典と根拠

ORDレコード
ord-0d8681e32826420da7d49e8f21226107
出典データセット
uspto-grants-2001_01
特許番号
US06174839B1

反応ノート

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