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

HRID 271421Notes

Reaction equation

HRID 271421 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.[F:26][C:27]([F:37])([F:36])[C:28]1[CH:35]=[CH:34][C:31]([CH2:32]Br)=[CH:30][CH:29]=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]([CH2:32][C:31]4[CH:30]=[CH:29][C:28]([C:27]([F:26])([F:36])[F:37])=[CH:35][CH:34]=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 1230621-(Bromomethyl)-4-(trifluoromethyl)benzeneHCID 587728337-(4-chlorophenyl)-5-(methylthio)-8-phenyl-[1,2,4]triazolo[4,3-c]pyrimidin-3(2H)-one

Product 1

HCID 159537057-(4-chlorophenyl)-5-(methylthio)-8-phenyl-2-(4-(trifluoromethyl)benzyl)-[1,2,4]triazolo[4,3-c]pyrimidin-3(2H)-oneYield 78.7%

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 4-trifluoromethylbenzyl bromide (77.7 mg, 0.33 mmol), followed by K2CO3 (74.5 mg, 0.54 mmol). The resulting mixture was stirred at room temperature for 5 h. Insoluble material was filtered off and the filtrate was purified by silica gel column chromatography eluted with ethyl acetate-hexanes, then lyophilized from 1,4-dioxane, to obtain the title compound (112 mg) as an off-white lyophilate. HPLC/MS: retention time=4.50 min, [M+H]30 =527.

Workup

  1. filtrationInsoluble material was filtered off
  2. customthe filtrate was purified by silica gel column chromatography
  3. washeluted with ethyl acetate-hexanes

Sources & evidence

ORD record
ord-95015e3c5fa94885aee32cda31821269
Source dataset
uspto-grants-2008_11
Patent number
US07452892B2

Reaction notes

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