3,5-Dimethylpiperidine → 4-(2-Butynyloxy)-5-fluoro-6-(3,5-dimethylpiperidino)pyrimidine

HRID 423161Notes

Reaction equation

HRID 423161 reaction equation
[CH2:1]([O:5][C:6]1[C:11]([F:12])=[C:10](F)[N:9]=[CH:8][N:7]=1)[C:2]#[C:3][CH3:4].[CH3:14][CH:15]1[CH2:20][CH:19]([CH3:21])[CH2:18][NH:17][CH2:16]1>C1(C)C=CC=CC=1>[CH2:1]([O:5][C:6]1[C:11]([F:12])=[C:10]([N:17]2[CH2:18][CH:19]([CH3:21])[CH2:20][CH:15]([CH3:14])[CH2:16]2)[N:9]=[CH:8][N:7]=1)[C:2]#[C:3][CH3:4]

Participants

4

Reactant 2

HCID 1182593,5-DimethylpiperidineHCID 596619664-(2-Butynyloxy)-5,6-difluoropyrimidine

Product 1

HCID 593411354-(2-Butynyloxy)-5-fluoro-6-(3,5-dimethylpiperidino)pyrimidineYield 75.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

0.53 g of 4-(2-butynyloxy)-5,6-difluoropyrimidine and 0.39 g of 3,5-dimethylpiperidine (mixture of about cis:trans=7:3) were added to 1 ml of toluene, then the mixture was stirred at room temperature for 30 minutes. Then the reaction mixture was subjected to silica gel column chromatography to obtain 0.6 g of 4-(2-butynyloxy)-5-fluoro-6-(3,5-dimethylpiperidino)pyrimidine (referred as the present compound (4) hereinafter).

Sources & evidence

ORD record
ord-a4988457a04448449077036bae890905
Source dataset
uspto-grants-2012_01
Patent number
US08101753B2

Reaction notes

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