Dimethyl Sulfoxide → 2-(2-Azido-1,1-difluoro-ethyl)-pyrimidine

HRID 1171071Notes

Reaction equation

HRID 1171071 reaction equation
[F:1][C:2]([C:6]1[N:11]=[CH:10][CH:9]=[CH:8][N:7]=1)([F:5])[CH2:3]I.[N-:12]=[N+:13]=[N-:14].[Na+].CS(C)=O>O>[N:12]([CH2:3][C:2]([C:6]1[N:11]=[CH:10][CH:9]=[CH:8][N:7]=1)([F:5])[F:1])=[N+:13]=[N-:14]

Participants

5

Reactant 3

HCID 679Dimethyl SulfoxideHCID 33557Sodium AzideHCID 58973005Pyrimidine, 2-(1,1-difluoro-2-iodoethyl)-

Product 1

HCID 866153122-(2-Azido-1,1-difluoro-ethyl)-pyrimidineYield 102.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
95 °C

Procedure

A mixture of 2-(1,1-difluoro-2-iodo-ethyl)-pyrimidine (841 mg, 3.11 mmol), as prepared in the previous step, NaN3 (338 mg, 5.19 mmol), and DMSO (2.35 mL) was stirred at 95° C. for 3 days. The reaction was then shaken with water (10 mL) and extracted with ether (3×8 mL). The organic layers were combined, dried (Na2SO4), and concentrated to give the intermediate 2-(2-azido-1,1-difluoro-ethyl)-pyrimidine as a clear yellow oil (591 mg) that was immediately used in the next step without further purification or characterization.

Workup

  1. extractionextracted with ether (3×8 mL)
  2. dry with materialdried (Na2SO4)
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-0725ab80f1fa456d891d9fd65f047081
Source dataset
uspto-grants-2010_11
Patent number
US07829584B2

Reaction notes

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