Dichloromethane → 4,5-Dimethyl-2-(4-methylphenyl)pyrimidine

HRID 1077836Notes

Reaction equation

HRID 1077836 reaction equation
[CH3:1][C:2]1[C:7]([CH3:8])=[C:6](Cl)[N:5]=[C:4]([C:10]2[CH:15]=[CH:14][C:13]([CH3:16])=[CH:12][CH:11]=2)[N:3]=1.C(N(CC)CC)C.C(Cl)Cl>[Pd].CO>[CH3:1][C:2]1[C:7]([CH3:8])=[CH:6][N:5]=[C:4]([C:10]2[CH:15]=[CH:14][C:13]([CH3:16])=[CH:12][CH:11]=2)[N:3]=1

Participants

6

Reactant 3

HCID 6344DichloromethaneHCID 8471TriethylamineHCID 194302834,5-Dimethyl-6-chloro-2-(4-methylphenyl)pyrimidine

Product 1

HCID 194302024,5-Dimethyl-2-(4-methylphenyl)pyrimidineYield 83.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 4,5-dimethyl-6-chloro-2-(4-methylphenyl)pyrimidine (6.2 g), triethylamine (3.2), and palladium on carbon (200 mg) in 100 ml of methanol was stirred overnight under hydrogen. Methylene chloride was added, the solid filtered off through celite, and solvent removed from the filtrate under reduced pressure. Tetrahydrofuran was added to the residue, and triethylamine hydrochloride filtered off. Solvent was removed from the filtrate under reduced pressure, giving 4.4 g of 4,5-dimethyl-2-(4-methylphenyl)pyrimidine, m.p. 114° C.

Workup

  1. filtrationthe solid filtered off through celite, and solvent
  2. customremoved from the filtrate under reduced pressure
  3. additionTetrahydrofuran was added to the residue, and triethylamine hydrochloride
  4. filtrationfiltered off
  5. customSolvent was removed from the filtrate under reduced pressure

Sources & evidence

ORD record
ord-b32b856a98264bdb8efc8602e4b085d5
Source dataset
uspto-grants-1996_08
Patent number
US05545645

Reaction notes

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