CID 406 → 5-Bromo-2-hydrazinopyrimidine
Reaction equation
P(=O)([O-])[O-].Br[C:6]1[N:11]=[CH:10][C:9]([Br:12])=[CH:8][N:7]=1.[NH2:13][NH2:14]>>[Br:12][C:9]1[CH:8]=[N:7][C:6]([NH:13][NH2:14])=[N:11][CH:10]=1Participants
4
Procedure
The preparation of phosphonates in which the phosphonate is attached by means of a pyrimidinyl group, either directly or with a saturated or unsaturated carbon chain is illustrated above. In this procedure, 2,5-dibromopyrimidine 132.32 (Chem. Lett., 1992, 583) is reacted with hydrazine to afford 5-bromo-2-pyrimidinyl hydrazine 132.33. The preparation of pyrimidinyl hydrazines by the reaction of 2-halopyrimidines with hydrazine is described in J. Med. Chem., 2002, 45, 5397. The product is then reacted with the ketoaldehyde 132.3 to yield the isomeric pyrazoles 132.34 and 132.35. The compound 132.34 is coupled, as described above, with a dialkyl phosphite to afford the phosphonate 132.37; basic hydrolysis then gives the triol 132.36.
Sources & evidence
- ORD record
- ord-ef306a61ef6a466da9f0659ed509ff8e
- Source dataset
- uspto-grants-2008_10
- Patent number
- US07432261B2
Reaction notes
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