Phenacyl bromide → 2-(5-Amino-7-(2-Furyl)-3H-[1,2,3]Triazolo[4,5-D]Pyrimidin-3-Yl)-1-Phenylethanone

HRID 733007Notes

Reaction equation

HRID 733007 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[C:7]2[NH:15][N:14]=[N:13][C:8]=2[N:9]=[C:10]([NH2:12])[N:11]=1.Br[CH2:17][C:18]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[O:19].C(N(CC)CC)C>CN(C=O)C.O>[NH2:12][C:10]1[N:11]=[C:6]([C:2]2[O:1][CH:5]=[CH:4][CH:3]=2)[C:7]2[N:15]=[N:14][N:13]([CH2:17][C:18]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=[O:19])[C:8]=2[N:9]=1

Participants

6

Reactant 3

HCID 6259Phenacyl bromideHCID 8471TriethylamineHCID 178508305HCID 178508305, compound

Product 1

HCID 98367342-(5-Amino-7-(2-Furyl)-3H-[1,2,3]Triazolo[4,5-D]Pyrimidin-3-Yl)-1-PhenylethanoneYield 13%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of 7-(2-furyl)-1H-[1,2,3]triazolo[4,5-d]pyrimidine-5-amine (101 mg, 0.5 mmol) in DMF (2 mL) was treated with 2-bromoacetophenone (100 mg, 0.5 mmol) and triethylamine (105 μL, 0.75 mmol), stirred at room temperature for 3 days, diluted with water (100 mL) and filtered. The resulting solid was purified by chromatography [SiO2; Hexane: EtOAc, (3:1 to 1:1)] to give the title compound (20 mg, 13%) as a yellow solid.

Workup

  1. filtrationfiltered
  2. customThe resulting solid was purified by chromatography [SiO2; Hexane: EtOAc, (3:1 to 1:1)]

Sources & evidence

ORD record
ord-c0e8e0ddd5614d9fa15668e37be559ce
Source dataset
uspto-grants-2009_09
Patent number
US07589097B2

Reaction notes

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