Allyl bromide → HCID 21874779, compound

HRID 733004Notes

Reaction equation

HRID 733004 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[C:7]2[N:15]=[N:14][N:13]([CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[C:19]([CH2:23][OH:24])[N:18]=3)[C:8]=2[N:9]=[C:10]([NH2:12])[N:11]=1.[H-].[Na+].[CH2:27](Br)[CH:28]=[CH2:29]>CN(C=O)C>[CH2:27]([O:24][CH2:23][C:19]1[N:18]=[C:17]([CH2:16][N:13]2[C:8]3[N:9]=[C:10]([N:12]([CH2:22][CH:17]=[CH2:16])[CH2:6][CH:2]=[CH2:3])[N:11]=[C:6]([C:2]4[O:1][CH:5]=[CH:4][CH:3]=4)[C:7]=3[N:15]=[N:14]2)[CH:22]=[CH:21][CH:20]=1)[CH:28]=[CH2:29]

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 24758Sodium hydrideHCID 21874543HCID 21874543, compound

Product 1

HCID 21874779HCID 21874779, compoundYield 59.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 7-(2-furyl)-3-(6-hydroxymethyl-2-pyridylmethyl)-3H-[1,2,3]triazolo[4,5-d]pyrimidine-5-amine (120 mg, 0.377 mmol) in DMF (5 mL) at 0° C. was treated with sodium hydride (30 mg, 0.743 mmol), stirred for 15 min, treated with allyl bromide (96 μl, 1.11 mmol), stirred at room temperature for 16 h, concentrated in vacuo to ˜2 mL and purified by chromatography [SiO2; isohexane:EtOAc (3:1)] to give the title compound (50 mg, 30%) as a yellow solid.

Workup

  1. stirringstirred at room temperature for 16 h
  2. concentrationconcentrated in vacuo to ˜2 mL
  3. custompurified by chromatography [SiO2; isohexane:EtOAc (3:1)]

Sources & evidence

ORD record
ord-86d364adae794560beeb9f6c2ccba792
Source dataset
uspto-grants-2009_09
Patent number
US07589097B2

Reaction notes

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