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

HRID 271409Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:13]=[CH:12][N:11]3[C:14](=[O:28])[N:15]([CH2:17][C:18]4[CH:19]=[N:20][C:21]([C:24]([F:27])([F:26])[F:25])=[CH:22][CH:23]=4)[N:16]=[C:10]3[CH:9]=2)=[CH:4][CH:3]=1.C(=O)([O-])[O-].[Ca+2].[Br-:34].[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>ClC(Cl)C>[Br:34][C:9]1[C:10]2[N:11]([C:14](=[O:28])[N:15]([CH2:17][C:18]3[CH:19]=[N:20][C:21]([C:24]([F:26])([F:25])[F:27])=[CH:22][CH:23]=3)[N:16]=2)[CH:12]=[N:13][C:8]=1[C:5]1[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=1

Participants

Conditions

Temperature: 70 °C

Procedure

To a solution of 7-(4-chlorophenyl)-2-((6-(trifluoromethyl)pyridin-3-yl)methyl)-[1,2,4]triazolo[4,3-c]pyrimidin-3(2H)-one (40.5 mg, 0.10 mmol) in dichloroethane (5 mL) at room temperature under argon was added calcium carbonate (10.0 mg, 0.10 mmol) and N,N,N-trimethyl-1-phenylmethanaminium tribromide (39.0 mg, 0.10 mmol). The resulting suspension was stirred and heated at 70° C. under argon for 2 h. Analysis by HPLC/MS indicated that most of the starting material had been consumed. After the reaction mixture was cooled to room temperature, the product was purified by silica gel column chromatography eluted with ethyl acetate-dichloromethane. This provided the title compound (43.6 mg) as a solid. HPLC/MS (methanol-water with 10 mM NH4OAc): retention time=3.67 min, [M+H]+486.

Workup

customhad been consumed
temperatureAfter the reaction mixture was cooled to room temperature
customthe product was purified by silica gel column chromatography
washeluted with ethyl acetate-dichloromethane

Sources & evidence

ORD record: ord-58b46b7875cc412ca3963ad5934bc234
Source dataset: uspto-grants-2008_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07452892B2

Reaction notes

Loading…