Ethyl bromoacetate → Ethyl 5-Amino-7-(2-Furyl)-3H-[1,2,3]Triazolo[4,5-D]Pyrimidin-3-Ylacetate

HRID 732974Notes

Reaction equation

HRID 732974 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]([O:20][CH2:21][CH3:22])=[O:19]>CN(C=O)C.CN(C1C=CN=CC=1)C>[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]([O:20][CH2:21][CH3:22])=[O:19])[C:8]=2[N:9]=1

Participants

5

Reactant 2

HCID 7748Ethyl bromoacetateHCID 178508305HCID 178508305, compound

Product 1

HCID 9921985Ethyl 5-Amino-7-(2-Furyl)-3H-[1,2,3]Triazolo[4,5-D]Pyrimidin-3-YlacetateYield 35%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 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 (4 mL) was treated with 4-(N,N-dimethylamino)pyridine (5 mg, 0.04 mmol) and ethyl bromoacetate (55 μL, 0.5 mmol), stirred at room temperature for 16 h and purified directly by chromatography [SiO2; EtOAc:Heptane (1:2)] to give the title compound (50 mg, 35%) as a white solid.

Workup

  1. custompurified directly by chromatography [SiO2; EtOAc:Heptane (1:2)]

Sources & evidence

ORD record
ord-fa0cf4c0d99c4a0c9bc8c80924294e3b
Source dataset
uspto-grants-2009_09
Patent number
US07589097B2

Reaction notes

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