Hydrazine → HCID 178478327, compound

HRID 1809660Notes

Reaction equation

HRID 1809660 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[N:16]=[C:15]([CH:17]=O)[CH:14]=[CH:13][CH:12]=1.[NH2:19][NH2:20]>>[Br:10][C:11]1[N:16]=[C:15]([C:17]2[C:2]3[C:3](=[N:4][C:5]([Cl:8])=[N:6][CH:7]=3)[NH:20][N:19]=2)[CH:14]=[CH:13][CH:12]=1

Participants

4

Reactant 3

HCID 9321HydrazineHCID 2899735-Bromo-2,4-dichloropyrimidineHCID 27570096-Bromopyridine-2-carbaldehyde

Product 1

HCID 178478327HCID 178478327, compound

Procedure

Alternatively, for compounds of formula Ia where X is N and Y is CH, in accordance to Scheme 2 below, 5-bromo-2,4-dichloro-pyrimidine (1) is reacted with 6-bromo-pyridine-2-carbaldehyde (3) by a Grignard reaction and the corresponding coupled alcohol is oxidized to the ketone. The ketone is reacted with hydrazine to give 3-(6-bromo-pyridin-2-yl)-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 Ia of this invention.

Sources & evidence

ORD record
ord-73e9508680d744d480f6616128021510
Source dataset
uspto-grants-2013_01
Patent number
US08362023B2

Reaction notes

Loading…