Phenol → 2-Phenoxypyrimidine
Reaction equation
S(=[C:4]1[N:9]=[CH:8][CH:7]=[CH:6][NH:5]1)(=O)=O.[C:10]1([OH:16])[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>>[O:16]([C:4]1[N:9]=[CH:8][CH:7]=[CH:6][N:5]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1Participants
Reactant 2
Product 1
Procedure
In step 1 of Scheme A, sulfanylpyrimidine compound a is treated with peracid or like oxidizing agent to afford sulfonylpyrimidine b. In step 2, sulfonylpyrimidine b is reacted with phenol compound c in the presence of base to provide phenoxypyrimidine compound d. Phenoxypyrimidine d is then treated with hydrazine in step 3 to yield hydrazinopyrimidine compound e. In step 4, hydrazinopyrimidine compound e undergoes a cyclization under basic conditions to afford a pyrazolone compound f. In step 5 the pyrazolone compound f is protected under basic conditions to give a protected pyrazol compound g. Partial deprotection of compound g in step 6 affords pyrazol compound h. In step 7 pyrazol compound h is reacted with alkylating agent i to give pyrazol ester compound j. In step 8 pyrazol ester i is deprotected to give a compound of formula II in accordance with the invention.
Sources & evidence
- ORD record
- ord-1587df9371954d788d0ee4da81d0c283
- Source dataset
- uspto-grants-2009_07
- Patent number
- US07563800B2
Reaction notes
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