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

HRID 22254Notes

Reaction equation

HRID 22254 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-(4methylphenyl)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-63fd8e3b9d414ca8a4f2ba5d8f6e2869
Source dataset
uspto-grants-1995_06
Patent number
US05428037

Reaction notes

Loading…