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New route to pyrimido[4,5‐ e ][1,3,4]thiadiazine derivatives
Author(s) -
Rahimizadeh M.,
Nikpour M.,
Bakavoli M.
Publication year - 2007
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570440230
Subject(s) - chemistry , carbon disulfide , acetonitrile , halide , pyrimidine , chloroform , alkyl , ethanol , methylhydrazine , medicinal chemistry , organic chemistry , combinatorial chemistry , stereochemistry , phenylhydrazine
5‐Bromo‐2‐chloro‐4‐methyl‐6‐(1‐methylhydrazino)pyrimidine is readily obtained from the recently reported 5‐bromo‐2,4‐dichloro‐6‐methylpyrimidine by treatment with methylhydrazine in chloroform. Treatment of this compound with carbon disulfide and several alkyl halides gave an intermediate which was successfully converted to its corresponding 3‐(alkylsulfanyl)‐7‐chloro‐1,5‐dimethyl‐1 H ‐pyrimido[4,5‐ e ][1,3,4]thiadiazine derivatives in basic acetonitrile. The latter compounds were reacted with secondary amines in boiling ethanol to afford the related 7‐amino derivatives.