Sodium borohydride → 6-(3,4-Dimethoxyphenyl)-3-methyl-1,2,3,4-tetrahydro-4-(2,4,6-trimethylphenylimino)pyrimidine

HRID 4338

Reaction equation

HRID 4338 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]2[N:16]=[CH: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].[BH4-].[Na+]>C(O)C.O>[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]

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 201522633,4-Dihydro-6-(3,4-dimethoxyphenyl)-3-methyl-4-(2,4,6-trimethylphenylimino)pyrimidine

Product 1

HCID 1357361726-(3,4-Dimethoxyphenyl)-3-methyl-1,2,3,4-tetrahydro-4-(2,4,6-trimethylphenylimino)pyrimidineYield 58.7%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a suspension of 3,4-dihydro-6-(3,4-dimethoxyphenyl)-3-methyl-4-(2,4,6-trimethylphenylimino)pyrimidine (2.0 g) in a mixture of ethanol (10 ml) and water (10 ml) was added sodium borohydride (1.04 g), and the mixture was stirred under reflux for 1.5 hours. After removal of the organic solvent, the mixture was suspended in water, and extracted with ethyl acetate. The organic layer was dried over magnesium sulfate, evaporated, and triturated in ethanol, to give 6-(3,4-dimethoxyphenyl)-3-methyl-1,2,3,4-tetrahydro-4-(2,4,6-trimethylphenylimino)pyrimidine (1.18 g).

Workup

  1. temperatureunder reflux for 1.5 hours
  2. customAfter removal of the organic solvent
  3. extractionextracted with ethyl acetate
  4. dry with materialThe organic layer was dried over magnesium sulfate
  5. customevaporated
  6. customtriturated in ethanol

Sources & evidence

ORD record
ord-49ae6795d91842138a9966c6c26eeb9a
Source dataset
uspto-grants-1988_02
Patent number
US04725600

Linked notes

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