Aminomethylation of pyrimidines

Citation
Vp. Krivonogov et al., Aminomethylation of pyrimidines, RUSS J ORG, 36(8), 2000, pp. 1219-1224
Citations number
11
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY
ISSN journal
10704280 → ACNP
Volume
36
Issue
8
Year of publication
2000
Pages
1219 - 1224
Database
ISI
SICI code
1070-4280(200008)36:8<1219:AOP>2.0.ZU;2-Q
Abstract
Aminomethylation of not yet described 5-hydroxy-6-methyluracil, 3-isobutylt kioethyl-6-methyluracil, and 4-amino-6-hydroxy-2-methylpyrimidine. The amin omethylation of 5-hydroxy-6-methyluracil with morpholine or piperidine occu rs in position 3 irrespective the ratio of original reagents whereas at an equivalent amount of piperazine it attacks position 3, and at excess both p ositions 3 and 1. The aminomethylation with an equivalent amount of piperaz ine occurs with 3-isobutylthioethyl-6-methyluracil and 4-amino-6-hydroxy-2- methylpyrimidine at position 5 of pyrimidines. At the ratio of 5-hydroxy-6- methyluracil, 3-isobutylthioethyl-6-methyluracil, or 4-amino-6-hydroxy-2-me thylpyrimidine : formaldehyde : piperazine equal to 2:2:1 forms 1,4-bis(5-p yrimidinylmethyl)piperazine.