Sodium hydride → HCID 178509772, compound

HRID 732994Notes

Reaction equation

HRID 732994 reaction equation
C[Si](C)(C)CCOC[N:7]1[C:11]([C:12]2[C:13]3[NH:21][N:20]=[N:19][C:14]=3[N:15]=[C:16]([NH2:18])[N:17]=2)=[CH:10][CH:9]=[N:8]1.[H-].[Na+].Br[CH2:27][C:28]1[CH:29]=[C:30]([CH:40]=[CH:41][CH:42]=1)[CH2:31][NH:32]C(=O)OC(C)(C)C>CN(C=O)C>[NH2:32][CH2:31][C:30]1[CH:29]=[C:28]([CH:42]=[CH:41][CH:40]=1)[CH2:27][N:19]1[C:14]2[N:15]=[C:16]([NH2:18])[N:17]=[C:12]([C:11]3[CH:10]=[CH:9][NH:8][N:7]=3)[C:13]=2[N:21]=[N:20]1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 21874548tert-Butyl {[3-(bromomethyl)phenyl]methyl}carbamateHCID 178504262HCID 178504262, compound

Product 1

HCID 178509772HCID 178509772, compoundYield 80.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A stirred solution of the 7-(1-(2-(trimethylsilyl)ethoxymethyl)-1H-pyrazol-5-yl)-1H-[1,2,3]triazolo[4,5-d]pyrimidine-5-amine (330 mg, 1 mmol) in dry DMF (5 mL) was treated with NaH (40 mg, 60% in oil, 1 mmol), stirred for 15 min, treated with tert-butyl N-(3-(bromomethyl)benzyl)carbamate (300 mg, 1 mmol) and stirred for 1 h. The mixture was partitioned between EtOAc (20 mL) and H2O (20 mL), the organic phase was dried (MgSO4), concentrated in vacuo and purified by chromatography [SiO2; iso-hexane:EtOAc (1:1)]. The resulting yellow syrup was dissolved in MeOH (3 mL), treated with HCl (2 mL, 4-M in dioxane), stirred for 17 h and the resulting solid filtered to give the title compound (258 mg, 80%) as a cream solid.

Workup

  1. stirringstirred for 1 h
  2. customThe mixture was partitioned between EtOAc (20 mL) and H2O (20 mL)
  3. dry with materialthe organic phase was dried (MgSO4)
  4. concentrationconcentrated in vacuo
  5. custompurified by chromatography [SiO2; iso-hexane:EtOAc (1:1)]
  6. dissolutionThe resulting yellow syrup was dissolved in MeOH (3 mL)
  7. additiontreated with HCl (2 mL, 4-M in dioxane)
  8. stirringstirred for 17 h
  9. filtrationthe resulting solid filtered

Sources & evidence

ORD record
ord-d75db728f3304b56ae3eb6a0a4565433
Source dataset
uspto-grants-2009_09
Patent number
US07589097B2

Reaction notes

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