Hydrazine → HCID 178478326, compound

HRID 1809661Notes

Reaction equation

Br[C:2]1[C:3](Cl)=[N:4][C:5]([Cl:8])=[N:6][CH:7]=1.[Br:10][C:11]1[CH:12]=[C:13]([CH:16]=[CH:17][CH:18]=1)[CH:14]=O.[NH2:19][NH2:20]>>[Br:10][C:11]1[CH:12]=[C:13]([C:14]2[C:2]3[C:3](=[N:4][C:5]([Cl:8])=[N:6][CH:7]=3)[NH:20][N:19]=2)[CH:16]=[CH:17][CH:18]=1

Participants

Reactant 3

HCID 9321Hydrazine

HCID 765833-Bromobenzaldehyde

HCID 2899735-Bromo-2,4-dichloropyrimidine

Product 1

HCID 178478326HCID 178478326, compound

Procedure

Alternatively, for compounds of formula Ib where X and Y are CH, in accordance to Scheme 3 below, 5-bromo-2,4-dichloro-pyrimidine (1) is reacted with 3-bromo-benzaldehyde (4) by a Grignard reaction and the corresponding coupled alcohol is oxidized to the ketone. The ketone is reacted with hydrazine to give 3-(3-bromo-phenyl)-6-chloro-1H-pyrazolo[3,4-d]pyrimidine. The remaining chloro group can then be replaced by reacting with the appropriate amine and the bromide can be displacement with the required amine under Buckwald conditions to give compounds Ib of this invention.

Sources & evidence

ORD record: ord-aef62ac29587452a9a6b8da7027f7210
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08362023B2

Reaction notes

Loading…