YAKUGAKU ZASSHI
Online ISSN : 1347-5231
Print ISSN : 0031-6903
ISSN-L : 0031-6903
Vitamin B1及び諸関係化合物の研究 第73報
Pyrimidine誘導体の合成研究 その2 Pyrimidine誘導体のMannich反応 (ii)
平野 弘米本 春生
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1956 年 76 巻 3 号 p. 234-239

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2-Methyl-4-amino-6-hydroxypyrimidine (I) undergoes Mannich reaction with formaldehyde and piperidine, even in aqueous alkali solution and forms 2-methyl-4-amino-5-piperidinomethyl-6-hydroxypyrimidine (II), but the use of an excess of formaldehyde and piperidine results in the formation of the bis (piperidinomethyl) compound (III) of (I). Examination of the chemical properties and ultraviolet absorption spectrum of the bis compound (III) indicated the compound to be 2-methyl-4-piperidinomethylamino-5-piperidinomethyl-1, 6-dihydropyrimid-6-one (IIIf) and, at the same time, (I) and (II) were assumed to be the 1, 6-dihydropyrimid-6-one compounds (Ia) and (II′). 2-Methyl-4-methylamino-1, 6-dihydropyrimid-6-one (VII), similar to the 4-amino compound (Ia), also undergoes Mannich reaction with formaldehyde and piperidine to form 2-methyl-4-methylamino-5-piperidinomethyl-1, 6-dihydropyrimid-6-one (VIII).

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© by the PHARMACEUTICAL SOCIETY OF JAPAN
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