Aminomalononitrile p-toluenesulphonate → 5-Methylpyrazin-2-amine

HRID 128141

Reaction equation

HRID 128141 reaction equation
O=[C:2]([CH3:6])[CH:3]=[N:4][OH:5].S(C1C=CC(C)=CC=1)(O)(=O)=O.[NH2:18][CH:19]([C:22]#[N:23])[C:20]#[N:21]>>[NH2:21][C:20]1[CH:19]=[N:18][C:2]([CH3:6])=[CH:3][N:4]=1.[NH2:23][C:22]1[C:19]([C:20]#[N:21])=[N:18][C:2]([CH3:6])=[CH:3][N+:4]=1[O-:5]

Participants

4

Reactant 2

HCID 563049Aminomalononitrile p-toluenesulphonateHCID 63992132-Oxopropanal-1-oxime

Product 2

HCID 3132155-Methylpyrazin-2-amineHCID 178430961HCID 178430961, compound

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.

Workup

  1. customprepared by the method of Ferris et al., J

Sources & evidence

ORD record
ord-3fda0521f6c046bc9ec2d64823cc8a8f
Source dataset
uspto-grants-1981_03
Patent number
USRE030563

Linked notes

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