Sodium Azide → HCID 46901747, compound

HRID 1868460Notes

Reaction equation

Cl[CH2:2][C:3]1[C:4]([CH3:25])=[N:5][C:6]2[N:7]([CH:17]=[C:18]([C:20]([O:22][CH2:23][CH3:24])=[O:21])[N:19]=2)[C:8]=1[C:9]1[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][C:10]=1[Cl:16].[N-:26]=[N+:27]=[N-:28].[Na+]>CN(C=O)C.CCOC(C)=O>[N:26]([CH2:2][C:3]1[C:4]([CH3:25])=[N:5][C:6]2[N:7]([CH:17]=[C:18]([C:20]([O:22][CH2:23][CH3:24])=[O:21])[N:19]=2)[C:8]=1[C:9]1[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][C:10]=1[Cl:16])=[N+:27]=[N-:28]

Participants

Conditions

Temperature: 50 °C

Procedure

To a stirred solution of crude ethyl 6-(chloromethyl)-5-(2,4-dichlorophenyl)-7-methylimidazo[1,2-a]pyrimidine-2-carboxylate (448 mg, 1.12 mmol) in DMF (5 mL) was added NaN3 (110 mg, 1.69 mmol). The reaction was heated to 50° C. for 1 h. After cooling, the reaction was diluted with EtOAc and extracted with H2O and brine before drying over MgSO4. Filtration and concentration under reduced pressure gave ethyl 6-(azidomethyl)-5-(2,4-dichlorophenyl)-7-methylimidazo[1,2-a]pyrimidine-2-carboxylate (450 mg, 100% crude yield) as a yellow oil.

Workup

temperatureAfter cooling
extractionextracted with H2O and brine
dry with materialbefore drying over MgSO4
filtrationFiltration and concentration under reduced pressure

Sources & evidence

ORD record: ord-733517a192204c109910243327836b46
Source dataset: uspto-grants-2009_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07635699B2

Reaction notes

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