Piperidine → 4-(2-Butynyloxy)-5-fluoro-6-piperidinopyrimidine

HRID 14514Notes

Reaction equation

HRID 14514 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].[NH:14]1[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1>C(O)C>[CH2:1]([O:5][C:6]1[C:11]([F:12])=[C:10]([N:14]2[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]2)[N:9]=[CH:8][N:7]=1)[C:2]#[C:3][CH3:4]

Participants

4

Reactant 2

HCID 8082PiperidineHCID 225997174-(2-Butynyloxy)-5-fluoro-6-chloropyrimidine

Product 1

HCID 593411384-(2-Butynyloxy)-5-fluoro-6-piperidinopyrimidineYield 99.2%

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, 0.38 g of piperidine was added therein, and the mixture was stirred for 7 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 0.37 g of 4-(2-butynyloxy)-5-fluoro-6-piperidinopyrimidine (hereinafter, referred to as Compound (2)).

Workup

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

Sources & evidence

ORD record
ord-d270f758becd48d19d8ee195ccff863a
Source dataset
uspto-grants-2010_06
Patent number
US07732448B2

Reaction notes

Loading…