Sodium hydride → HCID 21874651, compound

HRID 750537Notes

Reaction equation

HRID 750537 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.[H-].[Na+].Br[CH2:19][C:20]1[CH:35]=[CH:34][C:23]2[N:24]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[N:25]=[N:26][C:22]=2[CH:21]=1>CN(C=O)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]([CH2:19][C:20]3[CH:35]=[CH:34][C:23]4[N:24]([C:27]([O:29][C:30]([CH3:31])([CH3:33])[CH3:32])=[O:28])[N:25]=[N:26][C:22]=4[CH:21]=3)[C:8]=2[N:9]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 21874723HCID 21874723, compoundHCID 178508305HCID 178508305, compound

Product 1

HCID 21874651HCID 21874651, compoundYield 24%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of 7-(2-furyl)-1H-[1,2,3]triazolo[4,5-d]pyrimidine-5-amine (404 mg, 2 mmol) in DMF (4 mL) was treated with NaH (60% dispersion, 80 mg, 2 mmol), stirred at room temperature for 10 min, treated with a solution of tert-butyl 5-(bromomethyl)-1H-benzotriazole-1-carboxylate (as a mixture with the 6-bromomethyl regioisomer) (624 mg, 2 mmol) in DMF (2 mL) and stirred overnight. The mixture was concentrated in vacuo and purified by chromatography [SiO2, isohexane:EtOAc (2:1)] to give tert-butyl 5-(5-amino-7-(2-furyl)-3H-triazolo[4,5-d]pyrimidin-3-yl)methyl-1H-benzotriazol-1-carboxylate (135 mg, 24%) (as a mixture with the 6-substituted regioisomer) as a white solid.

Workup

  1. stirringstirred overnight
  2. concentrationThe mixture was concentrated in vacuo
  3. custompurified by chromatography [SiO2, isohexane:EtOAc (2:1)]

Sources & evidence

ORD record
ord-b1b2954125f541f98c2c61b0cfcadf45
Source dataset
uspto-grants-2008_07
Patent number
US07405219B2

Reaction notes

Loading…