3,5-Dimethylpiperidine → 4,5-Difluoro-6-(3,5-dimethylpiperidino)pyrimidine

HRID 2425939Notes

Reaction equation

HRID 2425939 reaction equation
F[C:2]1[C:7]([F:8])=[C:6]([F:9])[N:5]=[CH:4][N:3]=1.[CH3:10][CH:11]1[CH2:16][CH:15]([CH3:17])[CH2:14][NH:13][CH2:12]1>C1(C)C=CC=CC=1>[F:9][C:6]1[C:7]([F:8])=[C:2]([N:13]2[CH2:14][CH:15]([CH3:17])[CH2:16][CH:11]([CH3:10])[CH2:12]2)[N:3]=[CH:4][N:5]=1

Participants

4

Reactant 2

HCID 1182593,5-DimethylpiperidineHCID 35727644,5,6-Trifluoropyrimidine

Product 1

HCID 593411404,5-Difluoro-6-(3,5-dimethylpiperidino)pyrimidineYield 97.9%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

Into 6 ml of toluene solution of 0.5 g of 4,5,6-trifluoropyrimidine was added dropwise 1 ml toluene solution of 0.51 g of 3,5-dimethylpiperidine (cis/trans diastereomer=about 4/1) at 0° C., and the mixture was stirred for one-and-half hour at same temperature. The reaction mixture was subjected to silica gel column chromatography to obtain 0.83 g of 4,5-difluoro-6-(3,5-dimethylpiperidino)pyrimidine. This compound had the cis/trans diastereomers originated two methyls on the piperidine ring. The ratio of the cis/trans diastereomer was about 5/1.

Workup

  1. customhalf hour

Sources & evidence

ORD record
ord-593fa4f167d74f7dbe6f2bd0ce416466
Source dataset
uspto-grants-2011_06
Patent number
US07968537B2

Reaction notes

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