2,4-Dichloro-6-methyl-5-propylpyrimidine → 4-Chloro-6-methyl-5-propylpyrimidine

HRID 898701Notes

Reaction equation

HRID 898701 reaction equation
CC(O[Na])=O.[Cl:6][C:7]1[N:12]=[C:11]([Cl:13])[C:10]([CH2:14][CH2:15][CH3:16])=[C:9]([CH3:17])[N:8]=1>CCOC(C)=O.[Pd]>[Cl:6][C:7]1[N:12]=[CH:11][C:10]([CH2:14][CH2:15][CH3:16])=[C:9]([CH3:17])[N:8]=1.[Cl:13][C:11]1[C:10]([CH2:14][CH2:15][CH3:16])=[C:9]([CH3:17])[N:8]=[CH:7][N:12]=1.[CH3:17][C:9]1[N:8]=[CH:7][N:12]=[CH:11][C:10]=1[CH2:14][CH2:15][CH3:16]

Participants

7

Reactant 2

HCID 223131522,4-Dichloro-6-methyl-5-propylpyrimidineHCID 178418247HCID 178418247, compound

Product 3

HCID 223131564-Chloro-6-methyl-5-propylpyrimidineHCID 223131614-Methyl-5-propylpyrimidineHCID 223131622-Chloro-6-methyl-5-propyl-pyrimidine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

5% Pd/C (25 mg) and CH3COONa (820 mg, 10 mmol) are added to a solution of 2,4-dichloro-6-methyl-5-propyl-pyrimidine (1.02 g, 5 mmol) in EtOAc (25 ml). The mixture is then hydrogenated at 50 psi overnight. The catalyst is filtered and the solvent is removed in vacuo. Flash column chromatography of the residue on silica gel by 4:1 hexane, EtOAc provides 2-chloro-6-methyl-5-propyl-pyrimidine (LC-MS, M+1 171.7), 4-chloro-6-methyl-5-propyl-pyrimidine (LC-MS, M+1 171.7) and 6-methyl-5-propyl-pyrimidine (LC-MS, M+1 157.7) as 1:1:1.5 mixture, which is separated by HPLC.

Workup

  1. customis then hydrogenated at 50 psi overnight
  2. filtrationThe catalyst is filtered
  3. customthe solvent is removed in vacuo

Sources & evidence

ORD record
ord-dee30d17222d4720bce25c5177e7a536
Source dataset
uspto-grants-2008_04
Patent number
US07351826B2

Reaction notes

Loading…