3,5-Dimethylpiperidine → 4-(3,5-Dimethylpiperidino)-5-fluoro-6-(2-pentynyloxy)pyrimidine

HRID 2076848Notes

Reaction equation

HRID 2076848 reaction equation
Cl[C:2]1[C:7]([F:8])=[C:6]([O:9][CH2:10][C:11]#[C:12][CH2:13][CH3:14])[N:5]=[CH:4][N:3]=1.[CH3:15][CH:16]1[CH2:21][CH:20]([CH3:22])[CH2:19][NH:18][CH2:17]1>>[CH3:15][CH:16]1[CH2:21][CH:20]([CH3:22])[CH2:19][N:18]([C:2]2[C:7]([F:8])=[C:6]([O:9][CH2:10][C:11]#[C:12][CH2:13][CH3:14])[N:5]=[CH:4][N:3]=2)[CH2:17]1

Participants

3

Reactant 2

HCID 1182593,5-DimethylpiperidineHCID 593411204-Chloro-5-fluoro-6-(2-pentynyloxy)pyrimidine

Product 1

HCID 578246854-(3,5-Dimethylpiperidino)-5-fluoro-6-(2-pentynyloxy)pyrimidineYield 84.7%

Procedure

0.2 g of 4-chloro-5-fluoro-6-(2-pentynyloxy)pyrimidine and 0.32 g of 3,5-dimethylpiperidine (cis/trans=about 3/1) were mixed and left for 3 hours at room temperature. The reaction mixture was subjected to silica gel column chromatography to obtain 0.23 g of 4-(3,5-dimethylpiperidino)-5-fluoro-6-(2-pentynyloxy)pyrimidine (hereinafter, referred to as Compound (11)). Compound (11) had the cis/trans diastereomer originated two methyls on the piperidine ring. The ratio of the cis/trans diastereomer was about 3.8/1.

Sources & evidence

ORD record
ord-ecb73bfc4b5049abb7387eefba02db70
Source dataset
uspto-grants-2011_04
Patent number
US07928110B2

Reaction notes

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