Water → 1-Acetyl-6-(3,4-dimethoxyphenyl)-3-methyl-1,2,3,4-tetrahydro-4-(2,4,6-trimethylphenylimino)pyrimidine

HRID 4339Notes

Reaction equation

HRID 4339 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]2[NH:16][CH2:15][N:14]([CH3:17])[C:13](=[N:18][C:19]3[C:24]([CH3:25])=[CH:23][C:22]([CH3:26])=[CH:21][C:20]=3[CH3:27])[CH:12]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].[C:28](OC(=O)C)(=[O:30])[CH3:29].O>N1C=CC=CC=1>[C:28]([N:16]1[C:11]([C:5]2[CH:6]=[CH:7][C:8]([O:9][CH3:10])=[C:3]([O:2][CH3:1])[CH:4]=2)=[CH:12][C:13](=[N:18][C:19]2[C:24]([CH3:25])=[CH:23][C:22]([CH3:26])=[CH:21][C:20]=2[CH3:27])[N:14]([CH3:17])[CH2:15]1)(=[O:30])[CH3:29]

Participants

5

Reactant 3

HCID 962WaterHCID 7918Acetic AnhydrideHCID 1357361726-(3,4-Dimethoxyphenyl)-3-methyl-1,2,3,4-tetrahydro-4-(2,4,6-trimethylphenylimino)pyrimidine

Product 1

HCID 201522891-Acetyl-6-(3,4-dimethoxyphenyl)-3-methyl-1,2,3,4-tetrahydro-4-(2,4,6-trimethylphenylimino)pyrimidine

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 6-(3,4-dimethoxyphenyl)-3-methyl-1,2,3,4-tetrahydro-4-(2,4,6-trimethylphenylimino)pyrimidine (0.5 g) in pyridine (5 ml) was added acetic anhydride (1.0 ml), and the mixture was stirred at ambient temperature for 2.5 hours. The mixture was poured into water (150 ml) and extracted with chloroform. The organic layer was washed with brine, dried over sodium sulfate, and evaporated. The residue was chromatographed on silica gel eluting with chloroform to give 1-acetyl-6-(3,4-dimethoxyphenyl)-3-methyl-1,2,3,4-tetrahydro-4-(2,4,6-trimethylphenylimino)pyrimidine (0.22 g).

Workup

  1. extractionextracted with chloroform
  2. washThe organic layer was washed with brine
  3. dry with materialdried over sodium sulfate
  4. customevaporated
  5. customThe residue was chromatographed on silica gel eluting with chloroform

Sources & evidence

ORD record
ord-3616968c1a0f4c4397905a7c8fdd4da3
Source dataset
uspto-grants-1988_02
Patent number
US04725600

Reaction notes

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