2-Acetoxymethyl-3-methoxy-5-methylpyrazine

Methoxy-3,6-dimethylpyrazine 4-oxide (283) gave only 2-acetoxymethyl-3-methoxy-5-methylpyrazine (284) (neat AC2O, reflux, 1 h 88%) 324 in contrast, the homologous substrate, 2,5-dibenzyl-3-methoxypyrazine 1-oxide (285), gave a separable mixture of 2-(a-acetoxybenzyl)-5-benzyl-3-methoxy-pyrazine (286) and 2-acetoxy-3,6-dibenzyl-5-methoxypyrazine (287) (neat Ac20, reflux, 90 min 55 and 20%, respectively).312... 

Acetoxymethyl- -chloropyrazine 2-Acetoxymethyl-3,6-dichloro-5-methylpyrazine 2-Acetoxymethyl-3,6-dichloro-5-methylpyrazine 1-oxide 2-Acetoxymethyl-3-ethoxypyrazine 2-Acetoxymethyl-5-isobutyl-3-methoxypyrazine 2-Acetoxymethyl-5-isobutyl-3-methoxypyrazine 1-oxide 2-Acetoxymethyl-3-methoxy-5-methylpyrazine 2-Acetoxymethyl-5-methoxy-6-methylpyrazine 2-Acetoxymethyl-3-methoxy-5-methylpyrazine 1-oxide 2-Acetoxymethyl-3-methylpyrazine 2-Acetoxymethyl-5-methylpyrazine... 

Acetoxymethyl- (126) gave 2-hydroxymethyl-3-methoxy-5-methylpyrazine (127) (K2C03, MeOH—H20, 20°C, 24 h 89%).324... 

Dimethylamino-23-dimethylpyrazine 1-oxide in boiling acetic anhydride gave 2-acetoxymethyl-3-dimethylamino-5-methylpyrazine (793) which was not isolated but saponified directly to 3-dimethylamino-2-hydroxymethyl-5-methylpyrazine (793). 2-Amino-3-cyano-5-methylpyrazine 1,4-dioxide refluxed with (a) acetic anhydride gave 3-acetamido-2-cyano-5-hydroxy-6-methylpyrazine 1-oxide (532) and (6) sodium methoxide gave 3-amino-2-cyano-5-methoxy-6-methylpyrazine 1-oxide (532). 

---