Dimethylformamide → HCID 117696403, compound

HRID 2205289Notes

Reaction equation

HRID 2205289 reaction equation
[N-:1]=[N+:2]=[N-:3].[Na+].[CH3:5][C:6](OS(C)(=O)=O)([C:8]1[C:17]2[C:12](=[C:13]([CH3:18])[CH:14]=[CH:15][CH:16]=2)[N:11]=[CH:10][N:9]=1)[CH3:7].CN(C=O)C>C([O-])([O-])=O.[Na+].[Na+].CCOC(C)=O>[N:1]([C:6]([C:8]1[C:17]2[C:12](=[C:13]([CH3:18])[CH:14]=[CH:15][CH:16]=2)[N:11]=[CH:10][N:9]=1)([CH3:7])[CH3:5])=[N+:2]=[N-:3]

Participants

6

Reactant 3

HCID 6228DimethylformamideHCID 33557Sodium AzideHCID 117696401HCID 117696401, compound

Product 1

HCID 117696403HCID 117696403, compound

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 10340Sodium CarbonateSolvent

Procedure

Sodium azide (492 mg, 7.57 mmol) is added to methanesulfonic acid 1-methyl-1-(8-methyl-quinazolin-4-yl)-ethyl ester (680 mg, 78% content, 1.89 mmol) in DMF (1.5 mL, 19.56 mmol) and stirring is continued for 4 d. The reaction mixture is diluted with saturated Na2CO3 and EtOAc. The organic layer is washed with brine, dried and filtered to give 4-(1-azido-1-methyl-ethyl)-8-methyl-quinazoline (as a solution in EtOAc).

Workup

  1. washThe organic layer is washed with brine
  2. customdried
  3. filtrationfiltered

Sources & evidence

ORD record
ord-157839050b524bc1bea217ef7af4d054
Source dataset
uspto-grants-2016_06
Patent number
US09371282B2

Reaction notes

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