2-Methylpiperidine → 4-(2-Butynyloxy)-5-fluoro-6-(2-methylpiperidino)pyrimidine

HRID 14513

Reaction equation

HRID 14513 reaction equation
[CH2:1]([O:5][C:6]1[C:11]([F:12])=[C:10](Cl)[N:9]=[CH:8][N:7]=1)[C:2]#[C:3][CH3:4].[CH3:14][CH:15]1[CH2:20][CH2:19][CH2:18][CH2:17][NH:16]1>C(O)C>[CH2:1]([O:5][C:6]1[C:11]([F:12])=[C:10]([N:16]2[CH2:17][CH2:18][CH2:19][CH2:20][CH:15]2[CH3:14])[N:9]=[CH:8][N:7]=1)[C:2]#[C:3][CH3:4]

Participants

4

Reactant 2

HCID 79742-MethylpiperidineHCID 225997174-(2-Butynyloxy)-5-fluoro-6-chloropyrimidine

Product 1

HCID 593411154-(2-Butynyloxy)-5-fluoro-6-(2-methylpiperidino)pyrimidineYield 71.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Into 3 ml of ethanol was resolved 0.3 g of 4-(2-butynyloxy)-6-chloro-5-fluoropyrimidine, 0.45 g of 2-methylpyperidine was added therein, and the mixture was stirred for 5 hours under reflux condition. The reaction mixture was cooled to near room temperature and concentrated. The residue was subjected to silica gel column chromatography to obtain 0.28 g of 4-(2-butynyloxy)-5-fluoro-6-(2-methylpiperidino)pyrimidine (hereinafter, referred to as Compound (1)).

Workup

  1. additionwas added
  2. temperatureunder reflux condition
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-128a683dc56a4a128028ba8b3f713edc
Source dataset
uspto-grants-2010_06
Patent number
US07732448B2

Linked notes

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