Propargyl bromide → 3-(3-fluoro-4-(4-(prop-2-yn-1-yl)piperazin-1-yl)phenyl)-2,6-dimethylpyrimidin-4(3H)-one

HRID 56196Notes

Reaction equation

HRID 56196 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([N:14]2[C:19](=[O:20])[CH:18]=[C:17]([CH3:21])[N:16]=[C:15]2[CH3:22])[CH:5]=[CH:6][C:7]=1[N:8]1[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1.C([O-])([O-])=O.[K+].[K+].Br[CH2:30][C:31]#[CH:32]>CC#N>[F:1][C:2]1[CH:3]=[C:4]([N:14]2[C:19](=[O:20])[CH:18]=[C:17]([CH3:21])[N:16]=[C:15]2[CH3:22])[CH:5]=[CH:6][C:7]=1[N:8]1[CH2:9][CH2:10][N:11]([CH2:32][C:31]#[CH:30])[CH2:12][CH2:13]1

Participants

5

Reactant 3

HCID 7842Propargyl bromideHCID 11430Potassium CarbonateHCID 900231543-[3-Fluoro-4-(1-piperazinyl)phenyl]-2,6-dimethyl-4(3H)-pyrimidinone

Product 1

HCID 900230243-(3-fluoro-4-(4-(prop-2-yn-1-yl)piperazin-1-yl)phenyl)-2,6-dimethylpyrimidin-4(3H)-oneYield 44.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a suspension of 3-(3-fluoro-4-(piperazin-1-yl)phenyl)-2,6-dimethylpyrimidin-4(3H)-one (0.30 g, 1.00 mmol) and K2CO3 (0.69 g, 5.00 mmol) in CH3CN (15 mL) was added 3-bromoprop-1-yne (0.12 g, 1.01 mmol) and the mixture was stirred at rt for 36 h. The mixture was then filtered, and the filtrate was concentrated in vacuo. The residue was purified by a silica gel column chromatography (PE/EtOAc (V/V)=1:1) to give the title compound as a white solid (0.15 g, 44%). The compound was characterized by the following spectroscopic data:

Workup

  1. filtrationThe mixture was then filtered
  2. concentrationthe filtrate was concentrated in vacuo
  3. customThe residue was purified by a silica gel column chromatography (PE/EtOAc (V/V)=1:1)

Sources & evidence

ORD record
ord-d38557f23f964613bb73f2e16c57406a
Source dataset
uspto-grants-2016_09
Patent number
US09434695B2

Reaction notes

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