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

HRID 965684Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 965684
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]

Komponenten

7

Edukt 2

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

Produkt 3

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

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-7af81355057a464d8b137f1f49a68efb
Quelldatensatz
uspto-grants-2005_10
Patentnummer
US06951864B2

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