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

HRID 570865

反応式

HRID 570865 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]([O:21][CH3:22])(=[O:20])[CH2:16][C:17]([CH3:19])=O.C[Si](OP([O-])([O-])=O)(C)C.Cl.[CH2:33]1[CH2:37]O[CH2:35][CH2:34]1>>[CH3:22][O:21][C:15]([C:16]1[CH:35]([C:34]2[CH:2]=[CH:3][C:4]([C:5]#[N:9])=[CH:37][CH:33]=2)[NH:12][C:10](=[S:11])[N:9]([C:5]2[CH:6]=[CH:7][CH:8]=[C:3]([C:2]([F:1])([F:13])[F:14])[CH:4]=2)[C:17]=1[CH3:19])=[O:20]

参加物

6

反応物 5

HCID 313Hydrochloric AcidHCID 7757Methyl acetoacetateHCID 8028TetrahydrofuranHCID 7358443-(Trifluoromethyl)phenylthioureaHCID 18172808Trimethylsilylphosphate

生成物 1

HCID 57762471Methyl 4-(4-cyanophenyl)-6-methyl-2-thioxo-1-[3-(trifluoromethyl)phenyl]-1,2,3,4-tetrahydro-5-pyrimidinecarboxylate

反応条件

温度
70 °C

実験手順

To a solution of 3-trifluoromethylphenylthiourea (2.2 g, 10 mmol) 4-cyanobenzaldehyde (1.4 g, 11 mmol) and methyl acetoacetate (1.2 mL, 11 mmol) in THF (40 mL) was added trimethylsilylphosphate (1.8 g) and the mixture heated at 70° C. After 17 hours, the reaction mixture was allowed to cool, then poured onto 0.5 M HCl (200 mL) and extracted into EtOAc. The organic phase was washed with water, then brine, dried (Na2SO4) and concentrated in vacuo. The resulting residue was purified by silica gel chromatography eluting with a gradient of 20-30% EtOAc in cyclohexane Appropriate fractions were combined and concentrated in vacuo to yield the title compound as a white foam (3.7 g).

後処理

  1. temperatureto cool
  2. extractionextracted into EtOAc
  3. washThe organic phase was washed with water
  4. dry with materialbrine, dried (Na2SO4)
  5. concentrationconcentrated in vacuo
  6. customThe resulting residue was purified by silica gel chromatography
  7. washeluting with a gradient of 20-30% EtOAc in cyclohexane Appropriate fractions
  8. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-3578777d515d4a10b4fdb51e498dd236
出典データセット
uspto-grants-2015_05
特許番号
US09023855B2

関連ノート

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