1,2,3,6-Tetrahydropyridine → 3,4-Dihydro-6-(3,4-dimethoxyphenyl)-3-methyl-2-(1,2,3,6-tetrahydropyridin-1-yl)-4-(2,4,6-trimethylphenylimino)pyrimidine

HRID 4337

Reaction equation

HRID 4337 reaction equation
Cl[C:2]1[N:7]([CH3:8])[C:6](=[N:9][C:10]2[C:15]([CH3:16])=[CH:14][C:13]([CH3:17])=[CH:12][C:11]=2[CH3:18])[CH:5]=[C:4]([C:19]2[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[C:21]([O:27][CH3:28])[CH:20]=2)[N:3]=1.[NH:29]1[CH2:34][CH:33]=[CH:32][CH2:31][CH2:30]1>C(O)C>[CH3:28][O:27][C:21]1[CH:20]=[C:19]([C:4]2[N:3]=[C:2]([N:29]3[CH2:30][CH:31]=[CH:32][CH2:33][CH2:34]3)[N:7]([CH3:8])[C:6](=[N:9][C:10]3[C:15]([CH3:16])=[CH:14][C:13]([CH3:17])=[CH:12][C:11]=3[CH3:18])[CH:5]=2)[CH:24]=[CH:23][C:22]=1[O:25][CH3:26]

Participants

4

Reactant 2

HCID 127501,2,3,6-TetrahydropyridineHCID 201522932-Chloro-3,4-dihydro-6-(3,4-dimethoxyphenyl)-3-methyl-4-(2,4,6-trimethylphenylimino)pyrimidine

Product 1

HCID 201522533,4-Dihydro-6-(3,4-dimethoxyphenyl)-3-methyl-2-(1,2,3,6-tetrahydropyridin-1-yl)-4-(2,4,6-trimethylphenylimino)pyrimidine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a suspension of 2-chloro-3,4-dihydro-6-(3,4-dimethoxyphenyl)-3-methyl-4-(2,4,6-trimethylphenylimino)pyrimidine (2.08 g) in ethanol (20 ml) was added 1,2,3,6-tetrahydropyridine (1.38 ml), and refluxed for 1.5 hours. The resulting precipitates were collected, dissolved in chloroform, washed with aqueous sodium bicarbonate solution, and dried over magnesium sulfate. After evaporated, the residue was triturated with diisopropyl ether to give 3,4-dihydro-6-(3,4-dimethoxyphenyl)-3-methyl-2-(1,2,3,6-tetrahydropyridin-1-yl)-4-(2,4,6-trimethylphenylimino)pyrimidine (1.95 g).

Workup

  1. temperaturerefluxed for 1.5 hours
  2. customThe resulting precipitates
  3. customwere collected
  4. dissolutiondissolved in chloroform
  5. washwashed with aqueous sodium bicarbonate solution
  6. dry with materialdried over magnesium sulfate
  7. customAfter evaporated
  8. customthe residue was triturated with diisopropyl ether

Sources & evidence

ORD record
ord-76ac84f8bfe844fe8d9db859da230bc7
Source dataset
uspto-grants-1988_02
Patent number
US04725600

Linked notes

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