4,6-Dichloropyrimidine → 4-Chloro-6-(3,5-dimethylpiperidin-1-yl)pyrimidine

HRID 14566

Reaction equation

HRID 14566 reaction equation
Cl[C:2]1[CH:7]=[C:6]([Cl:8])[N:5]=[CH:4][N:3]=1.[CH3:9][CH:10]1[CH2:15][CH:14]([CH3:16])[CH2:13][NH:12][CH2:11]1>>[Cl:8][C:6]1[CH:7]=[C:2]([N:12]2[CH2:13][CH:14]([CH3:16])[CH2:15][CH:10]([CH3:9])[CH2:11]2)[N:3]=[CH:4][N:5]=1

Participants

3

Reactant 2

HCID 709434,6-DichloropyrimidineHCID 1182593,5-Dimethylpiperidine

Product 1

HCID 593411264-Chloro-6-(3,5-dimethylpiperidin-1-yl)pyrimidineYield 66%

Procedure

0.3 g of 4,6-dichloropyrimidine and 0.34 g of 3,5-dimethylpiperidine (cis/trans diastereomer=about 3/1) were mixed and left for 5 hours at room temperature. The reaction mixture was subjected to silica gel column chromatography to obtain 0.3 g of 4-chloro-6-(3,5-dimethylpiperidino)pyrimidine. This compound had the cis/trans diastereomer originated two methyls on the pyperidine ring. The ratio of the cis/trans diastereomer was about 3.1/1.

Sources & evidence

ORD record
ord-d6b2761139a1439abcd16946d8b3148b
Source dataset
uspto-grants-2010_06
Patent number
US07732448B2

Linked notes

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