Allyl bromide → HCID 21874779, compound

HRID 750531Notes

Reaction equation

HRID 750531 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-e06de09722184e7bbc4ab6adeffffe7f
Source dataset
uspto-grants-2008_07
Patent number
US07405219B2

Reaction notes

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