Ethyl Acetoacetate → Ethyl 4-(4-cyanophenyl)-6-methyl-2-thioxo-1-[3-(trifluoromethyl)phenyl]-1,2,3,4-tetrahydro-5-pyrimidinecarboxylate

HRID 230275

反応式

HRID 230275 の反応式
[F:1][C:2]([F:14])([F:13])[C:3]1[CH:4]=[C:5]([NH:9][C:10]([NH2:12])=[S:11])[CH:6]=[CH:7][CH:8]=1.[C:15]([C:17]1[CH:24]=[CH:23][C:20]([CH:21]=O)=[CH:19][CH:18]=1)#[N:16].[C:25]([O:31][CH2:32][CH3:33])(=[O:30])[CH2:26][C:27]([CH3:29])=O>C1COCC1>[C:15]([C:17]1[CH:24]=[CH:23][C:20]([CH:21]2[C:26]([C:25]([O:31][CH2:32][CH3:33])=[O:30])=[C:27]([CH3:29])[N:9]([C:5]3[CH:6]=[CH:7][CH:8]=[C:3]([C:2]([F:1])([F:13])[F:14])[CH:4]=3)[C:10](=[S:11])[NH:12]2)=[CH:19][CH:18]=1)#[N:16]

参加物

5

反応物 3

HCID 8868Ethyl AcetoacetateHCID 660424-CyanobenzaldehydeHCID 7358443-(Trifluoromethyl)phenylthiourea

生成物 1

HCID 57762441Ethyl 4-(4-cyanophenyl)-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

3-Trifluoromethylphenyl thiourea (3.00 g, 13.6 mmol), 4-cyanobenzaldehyde (3.57 g, 27.3 mmol) and ethyl acetoacetate (3.55 g, 27.3 mmol) are dissolved in 50 ml THF. Ethyl polyphosphate (4.50 g) is added and the reaction mixture is stirred at reflux temperature overnight. After cooling to room temperature, it is quenched with 50 ml of water and extracted with 100 ml ethyl acetate (2×). The combined organic layers are dried with sodium sulfate and the solvent is removed in vacua. The product is purified via preparative HPLC (RP18-column; eluent: acetonitrile-water, gradient 10:90 to 90:10).

後処理

  1. temperatureat reflux temperature overnight
  2. customit is quenched with 50 ml of water
  3. extractionextracted with 100 ml ethyl acetate (2×)
  4. dry with materialThe combined organic layers are dried with sodium sulfate
  5. customthe solvent is removed in vacua
  6. customThe product is purified via preparative HPLC (RP18-column; eluent: acetonitrile-water, gradient 10:90 to 90:10)

出典と根拠

ORDレコード
ord-75a4783c934b477b8d5d8631cc587d0f
出典データセット
uspto-grants-2009_07
特許番号
US07566723B2

関連ノート

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