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

HRID 271415Notes

Reaction equation

HRID 271415 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:13]=[C:12]([CH3:14])[N:11]3[C:15](=[O:29])[N:16]([CH2:18][C:19]4[CH:20]=[N:21][C:22]([C:25]([F:28])([F:27])[F:26])=[CH:23][CH:24]=4)[N:17]=[C:10]3[CH:9]=2)=[CH:4][CH:3]=1.C(=O)([O-])[O-].[Ca+2].[Br-:35].[Br-].[Br-].C[N+](C)(C)CC1C=CC=CC=1.C[N+](C)(C)CC1C=CC=CC=1.C[N+](C)(C)CC1C=CC=CC=1>ClCCl.CO>[Br:35][C:9]1[C:10]2[N:11]([C:15](=[O:29])[N:16]([CH2:18][C:19]3[CH:20]=[N:21][C:22]([C:25]([F:27])([F:26])[F:28])=[CH:23][CH:24]=3)[N:17]=2)[C:12]([CH3:14])=[N:13][C:8]=1[C:5]1[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=1

Participants

6

Reactant 3

HCID 10112Calcium CarbonateHCID 53442637BenzyltrimethylammoniumtribromideHCID 587728497-(4-chlorophenyl)-5-methyl-2-((6-(trifluoromethyl)pyridin-3-yl)methyl)-[1,2,4]triazolo[4,3-c]pyrimidin-3(2H)-one

Product 1

HCID 587728438-bromo-7-(4-chlorophenyl)-5-methyl-2-((6-(trifluoromethyl)pyridin-3-yl)methyl)-[1,2,4]triazolo[4,3-c]pyrimidin-3(2H)-oneYield 109.5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 7-(4-chlorophenyl)-5-methyl-2-((6-(trifluoromethyl)pyridin-3-yl)methyl)-[1,2,4]triazolo[4,3-c]pyrimidin-3(2H)-one (210 mg, 0.50 mmol) in dichloromethane (10 mL) and methanol (10 mL) at room temperature under argon was added calcium carbonate (50.0 mg, 0.50 mmol) and N,N,N-trimethyl-1-phenylmethanaminium tribromide (195 mg, 0.50 mmol). The resulting suspension was stirred and heated at 60° C. under argon for 1 h. Analysis by HPLC/MS indicated that the starting material had been consumed. The solvents were removed under reduced pressure, and water (25 mL) was added. After stirring at room temperature for 30 min, the solid product was collected by filtration and further washed with water (2×10 mL). After drying, the title compound (273 mg) was obtained as an off-white solid. HPLC/MS: retention time=3.84 min, [M+H]30 =500.

Workup

  1. customhad been consumed
  2. customThe solvents were removed under reduced pressure, and water (25 mL)
  3. additionwas added
  4. stirringAfter stirring at room temperature for 30 min
  5. filtrationthe solid product was collected by filtration
  6. washfurther washed with water (2×10 mL)
  7. customAfter drying

Sources & evidence

ORD record
ord-f9ca06d2cdf540d195f29123b4874886
Source dataset
uspto-grants-2008_11
Patent number
US07452892B2

Reaction notes

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