Potassium Carbonate → 7-(4-chlorophenyl)-5-(methylthio)-8-phenyl-2-((6-(trifluoromethyl)pyridin-3-yl)methyl)-[1,2,4]triazolo[4,3-c]pyrimidin-3(2H)-one

HRID 271420Notes

Reaction equation

HRID 271420 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:13]=[C:12]([S:14][CH3:15])[N:11]3[C:16](=[O:19])[NH:17][N:18]=[C:10]3[C:9]=2[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[CH:4][CH:3]=1.Cl[CH2:27][C:28]1[CH:29]=[CH:30][C:31]([C:34]([F:37])([F:36])[F:35])=[N:32][CH:33]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:13]=[C:12]([S:14][CH3:15])[N:11]3[C:16](=[O:19])[N:17]([CH2:27][C:28]4[CH:33]=[N:32][C:31]([C:34]([F:37])([F:35])[F:36])=[CH:30][CH:29]=4)[N:18]=[C:10]3[C:9]=2[C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 27738105-(Chloromethyl)-2-(trifluoromethyl)pyridineHCID 587728337-(4-chlorophenyl)-5-(methylthio)-8-phenyl-[1,2,4]triazolo[4,3-c]pyrimidin-3(2H)-one

Product 1

HCID 159537047-(4-chlorophenyl)-5-(methylthio)-8-phenyl-2-((6-(trifluoromethyl)pyridin-3-yl)methyl)-[1,2,4]triazolo[4,3-c]pyrimidin-3(2H)-oneYield 75.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 7-(4-chlorophenyl)-5-(methylthio)-8-phenyl-[1,2,4]triazolo[4,3-c]pyrimidin-3(2H)-one (100 mg, 0.27 mmol) in DMF (2 mL) at room temperature under argon was added 5-(chloromethyl)-2-(trifluoromethyl)pyridine (64.4 mg, 0.33 mmol), followed by K2CO3 (74.5 mg, 0.54 mmol). The resulting mixture was stirred at room temperature for 5 h. The crude product was purified by silica gel column chromatography eluted with ethyl acetate—hexanes, then lyophilized from 1,4-dioxane, to obtain the title compound (107.5 mg) as an off-white lyophilate. HPLC/MS: retention time=4.24 min, [M+H]30 =528.

Workup

  1. customThe crude product was purified by silica gel column chromatography
  2. washeluted with ethyl acetate—hexanes

Sources & evidence

ORD record
ord-fd7fa9e0af6240ee99528ee33ff4b41b
Source dataset
uspto-grants-2008_11
Patent number
US07452892B2

Reaction notes

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