Water → HCID 58981784, compound

HRID 1727943Notes

Reaction equation

HRID 1727943 reaction equation
[C:1]1([CH:7]([C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=2)[CH2:8][CH2:9][O:10][C:11]([C:13]2[CH:14]([C:35]3[CH:40]=[CH:39][CH:38]=[C:37]([Cl:41])[CH:36]=3)[N:15]=[C:16]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[NH:17][C:18]=2[CH2:19][O:20][CH2:21][CH2:22][CH:23]2[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]2)=[O:12])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.O>C1C=CC=CC=1>[C:42]1([CH:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH2:8][CH2:9][O:10][C:11]([C:13]2[C:14]([C:35]3[CH:40]=[CH:39][CH:38]=[C:37]([Cl:41])[CH:36]=3)=[N:15][C:16]([C:29]3[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=3)=[N:17][C:18]=2[CH2:19][O:20][CH2:21][CH2:22][CH:23]2[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]2)=[O:12])[CH:43]=[CH:44][CH:45]=[CH:46][CH:47]=1

Participants

4

Reactant 2

HCID 962WaterHCID 69070297HCID 69070297, compound

Product 1

HCID 58981784HCID 58981784, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

89.8 mg (0.14 mmol) of 4-(3-chlorophenyl)-6-[(2-cyclohexylethoxy)methyl]-2-phenyl-1,4-dihydropyrimidine-5-carboxylic acid 3,3-diphenylpropyl ester and 94.3 mg (0.42 mmol) of 2,3-dichloro-5,6-dicyano-1,4-benzochinon (DDQ) were refluxed in 20 ml of benzene for 3 hours. After adding water, the reaction mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and then concentrated under reduced pressure. The residue was purified by the silica gel chromatography (hexane/ethyl acetate=9/1) to obtain the title compound.

Workup

  1. extractionthe reaction mixture was extracted with ethyl acetate
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by the silica gel chromatography (hexane/ethyl acetate=9/1)

Sources & evidence

ORD record
ord-e830a7cc7c474eafbb2e8bc7f7c5dc80
Source dataset
uspto-grants-2009_02
Patent number
US07494989B2

Reaction notes

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