Hydrochloric Acid → Ethyl 4-(4-cyano-2-methylphenyl)-6-methyl-2-thioxo-1-[3-(trifluoromethyl)phenyl]-1,2,3,4-tetrahydro-5-pyrimidinecarboxylate

HRID 230284

反応式

HRID 230284 の反応式
[C:1]([C:3]1[CH:10]=[CH:9][C:6]([CH:7]=O)=[C:5]([CH3:11])[CH:4]=1)#[N:2].[F:12][C:13]([F:25])([F:24])[C:14]1[CH:15]=[C:16]([NH:20][C:21]([NH2:23])=[S:22])[CH:17]=[CH:18][CH:19]=1.O=[C:27]([CH3:34])[CH2:28][C:29]([O:31][CH2:32][CH3:33])=[O:30].C[Si](OP(=O)=O)(C)C.Cl>C1COCC1>[C:1]([C:3]1[CH:10]=[CH:9][C:6]([CH:7]2[C:28]([C:29]([O:31][CH2:32][CH3:33])=[O:30])=[C:27]([CH3:34])[N:20]([C:16]3[CH:17]=[CH:18][CH:19]=[C:14]([C:13]([F:12])([F:24])[F:25])[CH:15]=3)[C:21](=[S:22])[NH:23]2)=[C:5]([CH3:11])[CH:4]=1)#[N:2]

参加物

7

反応物 5

HCID 313Hydrochloric AcidHCID 8868Ethyl AcetoacetateHCID 7358443-(Trifluoromethyl)phenylthioureaHCID 109096954-Formyl-3-methylbenzonitrileHCID 16133246Trimethyl(phosphooxy)silane

生成物 1

HCID 57762430Ethyl 4-(4-cyano-2-methylphenyl)-6-methyl-2-thioxo-1-[3-(trifluoromethyl)phenyl]-1,2,3,4-tetrahydro-5-pyrimidinecarboxylate

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

4-Cyano-2-methylbenzaldehyde (200 mg, 1.38 mmol), 3-trifluoromethylphenyl thiourea (276 mg, 1.25 mmol), ethyl 3-oxobutanoate (179 mg, 1.38 mmol) and trimethylsilyl polyphosphate (225 mg) in 5 ml THF are stirred overnight at reflux temperature. The reaction mixture is cooled to room temperature, and after addition of 20 ml 0.5 M hydrochloric acid the aqueous phase is extracted with ethyl acetate (2×20 ml). The combined organic layers are washed with saturated aqueous sodium carbonate solution and dried with sodium sulfate. The solvent is removed in vacuo and the crude product is purified via preparative HPLC (RP18-column; eluent: aceto-nitrile-water, gradient 10:90 to 90:10).

後処理

  1. temperatureat reflux temperature
  2. extractionis extracted with ethyl acetate (2×20 ml)
  3. washThe combined organic layers are washed with saturated aqueous sodium carbonate solution
  4. dry with materialdried with sodium sulfate
  5. customThe solvent is removed in vacuo
  6. customthe crude product is purified via preparative HPLC (RP18-column; eluent: aceto-nitrile-water, gradient 10:90 to 90:10)

出典と根拠

ORDレコード
ord-509619a7c4b04077b6a0c0fc2300104a
出典データセット
uspto-grants-2009_07
特許番号
US07566723B2

関連ノート

読み込み中…