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

HRID 965684Notes

Reaction equation

HRID 965684 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 hydrogenated at 50 psi overnight. The catalyst is filtered and the solvent 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 a 1:1:1.5 mixture.

Workup

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

Sources & evidence

ORD record
ord-7af81355057a464d8b137f1f49a68efb
Source dataset
uspto-grants-2005_10
Patent number
US06951864B2

Reaction notes

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