Sodium Azide → HCID 86758760, compound

HRID 2300844Notes

Reaction equation

HRID 2300844 reaction equation
[C:1]1([C@@H:7]([NH:9][C:10]2[N:15]=[C:14]([N:16]3[C:20]4[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=4[N:18]=[CH:17]3)[CH:13]=[C:12](Cl)[N:11]=2)[CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[N-:26]=[N+:27]=[N-:28].[Na+]>CN(C=O)C.CCOC(C)=O>[C:1]1([C@@H:7]([NH:9][C:10]2[N:15]=[C:14]([N:16]3[C:20]4[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=4[N:18]=[CH:17]3)[CH:13]=[C:12]([N:26]=[N+:27]=[N-:28])[N:11]=2)[CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 2

HCID 33557Sodium AzideHCID 86758759HCID 86758759, compound

Product 1

HCID 86758760HCID 86758760, compoundYield 85.6%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of of 2-[(S)-1-phenylethylamino]-4-[benzimidazol-1-yl]-6-chloropyrimidine (EXAMPLE 306 Step B) (55.8 mg, 0.16 mmol) in DMF (1 mL) was added sodium azide (16 mg, 0.24 mmol) and the mixture was heated at 80° C. for 7 h. It was cooled and diluted with EtOAc, then the organic layer was washed with H2O followed by brine. The organic extract was dried over Na2SO4, and the crude material was purified by flash chromatography using 1:3 EtOAc:hexane to yield 48.8 mg of the title compound. Mass spectrum 357.1 (CI, M+1).

Workup

  1. temperatureIt was cooled
  2. washthe organic layer was washed with H2O
  3. extractionThe organic extract
  4. dry with materialwas dried over Na2SO4
  5. customthe crude material was purified by flash chromatography

Sources & evidence

ORD record
ord-81375957a1024224b73355b3de29666c
Source dataset
uspto-grants-2002_12
Patent number
US06498165B1

Reaction notes

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