Potassium Carbonate → 2-[4-chloro-2-fluoro-5-(2-pyrimidyloxy)phenyl]hexahydro-3-thioxo-1H-[1,2,4]triazolo[1,2-a]pyridazin-1-one

HRID 1953987Notes

Reaction equation

HRID 1953987 reaction equation
[Cl:1][C:2]1[C:7]([OH:8])=[CH:6][C:5]([N:9]2[C:17](=[O:18])[N:12]3[CH2:13][CH2:14][CH2:15][CH2:16][N:11]3[C:10]2=[S:19])=[C:4]([F:20])[CH:3]=1.Cl[C:22]1[N:27]=[CH:26][CH:25]=[CH:24][N:23]=1.C(=O)([O-])[O-].[K+].[K+]>CS(C)=O>[Cl:1][C:2]1[C:7]([O:8][C:22]2[N:27]=[CH:26][CH:25]=[CH:24][N:23]=2)=[CH:6][C:5]([N:9]2[C:17](=[O:18])[N:12]3[CH2:13][CH2:14][CH2:15][CH2:16][N:11]3[C:10]2=[S:19])=[C:4]([F:20])[CH:3]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 744042-ChloropyrimidineHCID 133922772-(4-Chloro-2-fluoro-5-hydroxyphenyl)hexahydro-3-thioxo-1H-[1,2,4]triazolo[1,2-a]pyridazin-1-one

Product 1

HCID 184029602-[4-chloro-2-fluoro-5-(2-pyrimidyloxy)phenyl]hexahydro-3-thioxo-1H-[1,2,4]triazolo[1,2-a]pyridazin-1-oneYield 55%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
100 °C

Procedure

2-(4-Chloro-2-fluoro-5-hydroxyphenyl)hexahydro-3-thioxo-1H-[1,2,4]triazolo-[1,2-a]pyridazin-1-one (0.5 g) was mixed with 2-chloropyrimidine (1 equiv) and potassium carbonate (2 equiv) in dimethylsulfoxide (20 ml) and the resulting mixture stirred at 100° C. for 1.5 hour and at room temperature overnight. The mixture was processed and the residue column chromatographed (silica gel, methylene chloride:ethyl acetate, 3:1). to give the product (0.34 g, 55%). 1H NMR (CDCl3, TMS): 1.92(4H, m), 3.69(2H, m), 3.99(2H, m), 7.05(1H, m), 7.37(1H, d, J=6.5 Hz), 7.39(1H, d, J=9.0 Hz), 8.53(2H, d, J=4.8 Hz).

Workup

  1. customthe residue column chromatographed (silica gel, methylene chloride:ethyl acetate, 3:1)

Sources & evidence

ORD record
ord-539861564c724837a3981c012d09d45c
Source dataset
uspto-grants-2000_09
Patent number
US06121201

Reaction notes

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