2-(Bromomethyl)-1-methoxy-4-nitrobenzene → 7-(2-Furyl)-3-(2-methoxy-5-nitrobenzyl)-3H-[1,2,3]triazolo[4,5-d]pyrimidine-5-amine

HRID 750516Notes

Reaction equation

HRID 750516 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.[CH3:16][O:17][C:18]1[CH:25]=[CH:24][C:23]([N+:26]([O-:28])=[O:27])=[CH:22][C:19]=1[CH2:20]Br>CN(C=O)C.O>[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[C:7]2[N:15]=[N:14][N:13]([CH2:20][C:19]3[CH:22]=[C:23]([N+:26]([O-:28])=[O:27])[CH:24]=[CH:25][C:18]=3[O:17][CH3:16])[C:8]=2[N:9]=[C:10]([NH2:12])[N:11]=1

Participants

5

Reactant 2

HCID 775162-(Bromomethyl)-1-methoxy-4-nitrobenzeneHCID 178508305HCID 178508305, compound

Product 1

HCID 218745327-(2-Furyl)-3-(2-methoxy-5-nitrobenzyl)-3H-[1,2,3]triazolo[4,5-d]pyrimidine-5-amineYield 25.3%

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 (606 mg, 3 mmol) in DMF (5 mL) at 0° C., was treated with CsCO3 (977 mg, 3 mmol), stirred for 1 h, treated with 2-methoxy-5-nitrobenzyl bromide (738 mg, 3 mmol) and stirred at room temperature for 1 h. The reaction mixture was diluted with water (10 mL), filtered and the resulting solid purified by chromatography [SiO2; EtOAc:Heptane (2:1)] to give the title compound (279 mg, 25%) as a yellow solid.

Workup

  1. stirringstirred at room temperature for 1 h
  2. filtrationfiltered
  3. customthe resulting solid purified by chromatography [SiO2; EtOAc:Heptane (2:1)]

Sources & evidence

ORD record
ord-1f3260e6baf24021a6170d944640bb50
Source dataset
uspto-grants-2008_07
Patent number
US07405219B2

Reaction notes

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