(3-Trifluoromethylphenyl)urea → Allyl 4-(4-cyanophenyl)-6-methyl-2-oxo-1-[3-(trifluoromethyl)phenyl]-1,2,3,4-tetrahydropyrimidine-5-carboxylate

HRID 1798843

反応式

HRID 1798843 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])=[O: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][CH:33]=[CH2:34])(=[O:30])[CH2:26][C:27]([CH3:29])=O>O1CCOCC1>[C:15]([C:17]1[CH:24]=[CH:23][C:20]([CH:21]2[C:26]([C:25]([O:31][CH2:32][CH:33]=[CH2:34])=[O:30])=[C:27]([CH3:29])[N:9]([C:5]3[CH:6]=[CH:7][CH:8]=[C:3]([C:2]([F:13])([F:14])[F:1])[CH:4]=3)[C:10](=[O:11])[NH:12]2)=[CH:19][CH:18]=1)#[N:16]

参加物

5

反応物 3

HCID 25712(3-Trifluoromethylphenyl)ureaHCID 660424-CyanobenzaldehydeHCID 70701Allyl acetoacetate

生成物 1

HCID 59684802Allyl 4-(4-cyanophenyl)-6-methyl-2-oxo-1-[3-(trifluoromethyl)phenyl]-1,2,3,4-tetrahydropyrimidine-5-carboxylate

試薬・触媒・溶媒 1

HCID 312751,4-Dioxane溶媒

実験手順

45.0 g ethyl polyphosphate are dissolved in 150 ml dioxane, 15.0 g (73.5 mmol) N-[3-(trifluoro-methyl)phenyl]urea, 19.3 g (147 mmol) 4-cyanobenzaldehyde and 20.9 g (147 mmol) allyl acetoacetate are added, and the mixture is stirred under reflux overnight. Volatiles are evaporated in vacuo, the remainder is dissolved in ethyl acetate and sequentially washed with saturated sodium hydrogencarbonate, sodium hydrogensulfite and sodium chloride solution. The organic phase is dried over magnesium sulfate, filtered and evaporated to dryness in vacuo. The crude product is purified by column chromatography over silica gel (eluent: cyclohexane/ethyl acetate).

後処理

  1. temperatureunder reflux overnight
  2. customVolatiles are evaporated in vacuo
  3. dissolutionthe remainder is dissolved in ethyl acetate
  4. washsequentially washed with saturated sodium hydrogencarbonate, sodium hydrogensulfite and sodium chloride solution
  5. dry with materialThe organic phase is dried over magnesium sulfate
  6. filtrationfiltered
  7. customevaporated to dryness in vacuo
  8. customThe crude product is purified by column chromatography over silica gel (eluent: cyclohexane/ethyl acetate)

出典と根拠

ORDレコード
ord-6117047167004337af8f329ef4c43977
出典データセット
uspto-grants-2013_01
特許番号
US08343987B2

関連ノート

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