Water → 5-Azido-7-(cyclopropylamino)pyrazolo[1,5-a]pyrimidine-3-carbaldehyde

HRID 624831Notes

Reaction equation

Cl[C:2]1[CH:7]=[C:6]([NH:8][CH:9]2[CH2:11][CH2:10]2)[N:5]2[N:12]=[CH:13][C:14]([CH:15]=[O:16])=[C:4]2[N:3]=1.[N-:17]=[N+:18]=[N-:19].[Na+].O>CN(C)C=O>[N:17]([C:2]1[CH:7]=[C:6]([NH:8][CH:9]2[CH2:11][CH2:10]2)[N:5]2[N:12]=[CH:13][C:14]([CH:15]=[O:16])=[C:4]2[N:3]=1)=[N+:18]=[N-:19]

Participants

Conditions

Temperature: 80 °C

Procedure

To 5-chloro-7-(cyclopropylamino)pyrazolo[1,5-a]pyrimidine-3-carbaldehyde (4.0 g, 16.87 mmol) in dimethylformamide was added sodium azide (1.56 g, 23.9 mmol) and the reaction mixture was heated at 80° C. for 8 hrs. Cooled the reaction mixture, added water and white precipitate filtered and dried to yield 5-azido-7-(cyclopropylamino)pyrazolo[1,5-a]pyrimidine-3-carbaldehyde (2.95 g, 75% yield). LCMS (M+1=244)

Workup

temperatureCooled the reaction mixture
filtrationfiltered
customdried

Sources & evidence

ORD record: ord-d49d4370bc5c4486848ea2bb2d3b1ea7
Source dataset: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09303033B2

Reaction notes

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