Propargyl bromide → 1-[4-chloro-2-fluoro-5-(2-propynyloxy)-phenyl]-2-propoxy-4-trifluoromethyl-6(1H)-pyrimidinone

HRID 1193915Notes

Reaction equation

HRID 1193915 reaction equation
[Cl:1][C:2]1[C:7]([OH:8])=[CH:6][C:5]([N:9]2[C:14](=[O:15])[CH:13]=[C:12]([C:16]([F:19])([F:18])[F:17])[N:11]=[C:10]2[O:20][CH2:21][CH2:22][CH3:23])=[C:4]([F:24])[CH:3]=1.[CH2:25](Br)[C:26]#[CH:27].C(=O)([O-])[O-].[Na+].[Na+]>CC(C)=O>[Cl:1][C:2]1[C:7]([O:8][CH2:27][C:26]#[CH:25])=[CH:6][C:5]([N:9]2[C:14](=[O:15])[CH:13]=[C:12]([C:16]([F:18])([F:17])[F:19])[N:11]=[C:10]2[O:20][CH2:21][CH2:22][CH3:23])=[C:4]([F:24])[CH:3]=1

Participants

5

Reactant 3

HCID 7842Propargyl bromideHCID 10340Sodium CarbonateHCID 212707161-(4-chloro-2-fluoro-5-hydroxyphenyl)-2-propoxy-4-trifluoromethyl-6(1H)-pyrimidinone

Product 1

HCID 539812251-[4-chloro-2-fluoro-5-(2-propynyloxy)-phenyl]-2-propoxy-4-trifluoromethyl-6(1H)-pyrimidinone

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

using 1-(4-chloro-2-fluoro-5-hydroxyphenyl)-2-propoxy-4-trifluoromethyl-6(1H)-pyrimidinone and propargyl bromide with sodium carbonate in acetone there is obtained 1-[4-chloro-2-fluoro-5-(2-propynyloxy) -phenyl]-2-propoxy-4-trifluoromethyl-6(1H)-pyrimidinone, 1H-NMR (CDCl3, 400 MHz): 7.34 ppm (d,1H), 6.98 ppm (d,1H), 6.60 ppm (s,1H), 4.76 ppm (m,2H), 4.39 ppm (m,2H), 2.56 ppm (t,1H), 1.67 ppm (m,2H), 0.85 ppm (t,3H);

Sources & evidence

ORD record
ord-66c994fe24fb4176bcffe012f4759164
Source dataset
uspto-grants-1989_03
Patent number
US04812164

Reaction notes

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