Phosphorus trichloride → 3-Amino-6-methylpyrazine-2-carbonitrile
Reaction equation
[NH2:1][C:2]1[C:7]([C:8]#[N:9])=[N:6][C:5]([CH3:10])=[CH:4][N+:3]=1[O-].P(Cl)(Cl)Cl>>[NH2:1][C:2]1[C:7]([C:8]#[N:9])=[N:6][C:5]([CH3:10])=[CH:4][N:3]=1Participants
3
Procedure
The intermediate 2-amino-5-methylpyrazine is prepared stepwise, starting with 2-oxopropanal 1-oxime. This oxime is allowed to react with aminomalononitrile tosylate [prepared by the method of Ferris et al., J. Am. Chem. Soc. 88, 3829 (1966)], to yield 2-amino-3-cyano-5-methylpyrazine 1-oxide. The pyrazine 1-oxide prepared in this manner is allowed to react with phosphorous trichloride to yield 2-amino-3-cyano-5-methylpyrazine. This 2-amino-3-cyano-5-methylpyrazine is hydrolyzed with aqueous sodium hydroxide to yield 2-amino-3-carboxy-5-methylpyrazine, which, when heated in tetrahydronaphthalene, is decarboxylated to yield the desired 2-amino-5-methylpyrazine.
Sources & evidence
- ORD record
- ord-4415bb65f675437084c4d85c56cae929
- Source dataset
- uspto-grants-1981_03
- Patent number
- USRE030563
Reaction notes
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