Methyl iodide → 2-Benzylimino-6-(3,4-dimethoxyphenyl)-1,3-dimethyl-1,2,3,4-tetrahydro-4-(2,4,6-trimethylphenylimino)pyrimidine

HRID 4334

Reaction equation

HRID 4334 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]2[N:16]=[C:15]([N:17](C)[CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[N:14]([CH3:26])[C:13](=[N:27][C:28]3[C:33]([CH3:34])=[CH:32][C:31]([CH3:35])=[CH:30][C:29]=3[CH3:36])[CH:12]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].[CH3:37]I>O1CCCC1>[CH2:18]([N:17]=[C:15]1[N:14]([CH3:26])[C:13](=[N:27][C:28]2[C:29]([CH3:36])=[CH:30][C:31]([CH3:35])=[CH:32][C:33]=2[CH3:34])[CH:12]=[C:11]([C:5]2[CH:6]=[CH:7][C:8]([O:9][CH3:10])=[C:3]([O:2][CH3:1])[CH:4]=2)[N:16]1[CH3:37])[C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

Participants

4

Reactant 2

HCID 6328Methyl iodideHCID 201522733,4-dihydro-6-(3,4-dimethoxyphenyl)-3-methyl-2-(N-methyl-N-benzylamino)-4-(2,4,6-trimethylphenylimino)pyrimidine

Product 1

HCID 201522602-Benzylimino-6-(3,4-dimethoxyphenyl)-1,3-dimethyl-1,2,3,4-tetrahydro-4-(2,4,6-trimethylphenylimino)pyrimidine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3,4-dihydro-6-(3,4-dimethoxyphenyl)-3-methyl-2-(N-methyl-N-benzylamino)-4-(2,4,6-trimethylphenylimino)pyrimidine (1.0 g) in tetrahydrofuran (20 ml) was added methyl iodide (2.58 ml). The solution was refluxed for 10 hours and cooled to ambient temperature. The reaction mixture was evaporated in vacuo and the residue was chromatographed on silica gel using chloroform to give 2-benzylimino-6-(3,4-dimethoxyphenyl)-1,3-dimethyl-1,2,3,4-tetrahydro-4-(2,4,6-trimethylphenylimino)pyrimidine (0.62 g).

Workup

  1. temperatureThe solution was refluxed for 10 hours
  2. customThe reaction mixture was evaporated in vacuo
  3. customthe residue was chromatographed on silica gel

Sources & evidence

ORD record
ord-19fb07c87ee04a17a744052b6bbc4bb6
Source dataset
uspto-grants-1988_02
Patent number
US04725600

Linked notes

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