Sodium hydride → HCID 9922633, compound

HRID 733009Notes

Reaction equation

HRID 733009 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+].C[Si](C)(C)CCOC[O:24][C:25]1[CH:32]=[CH:31][C:28]([CH2:29]Br)=[CH:27][CH:26]=1>CN(C=O)C>[OH:24][C:25]1[CH:32]=[CH:31][C:28]([CH2:29][N:13]2[C:8]3[N:9]=[C:10]([NH2:12])[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:27][CH:26]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 10969145HCID 10969145, compoundHCID 178508305HCID 178508305, compound

Product 1

HCID 9922633HCID 9922633, compoundYield 7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 7-(2-furyl)-1H-[1,2,3]triazolo[4,5-d]pyrimidine-5-amine (400 mg, 1.98 mmol) in DMF (3 mL), at 0° C., was treated with 60% sodium hydride in mineral oil (80 mg, 1.98 mmol), stirred for 30 min, treated with 4-(2-(trimethylsilyl)ethoxymethoxy)benzyl bromide (1.23 g, 3.96 mmol), stirred at room temperature for 48 h and purified by chromatography [SiO2; EtOAc: heptane, (1:2)]. The resulting yellow solid was dissolved in MeOH:DMF (1:2), passed through an ion exchange cartridge (Isolute SPE SCX-2), concentrated in vacuo, and washed with water and ether to give the title compound (41 mg, 7%) as a pale yellow solid.

Workup

  1. stirringstirred at room temperature for 48 h
  2. custompurified by chromatography [SiO2; EtOAc: heptane, (1:2)]
  3. dissolutionThe resulting yellow solid was dissolved in MeOH:DMF (1:2)
  4. concentrationconcentrated in vacuo
  5. washwashed with water and ether

Sources & evidence

ORD record
ord-8b343d181e294e9ebee83ef4bd726c39
Source dataset
uspto-grants-2009_09
Patent number
US07589097B2

Reaction notes

Loading…