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The synthesis and structure of 5‐hydroxy‐2‐methyl‐2‐(2‐pyridinyl)hexahydro‐1,3‐pyrimidine
Author(s) -
Fenton David E.,
Moody Richard,
Casellato Umberto,
Vigato P. A.,
Graziani Rodolfo
Publication year - 1985
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.5570220634
Subject(s) - chemistry , monoclinic crystal system , pyrimidine , molecule , pyridine , hydrogen bond , crystal structure , stereochemistry , crystallography , molar ratio , medicinal chemistry , organic chemistry , catalysis
The synthesis and the x‐ray structure of 5‐hydroxy‐2‐methyl‐(2‐pyridinyl)hexahydro‐1,3‐pyrimidine are reported. The compound was prepared by reaction of 2‐acetylpyridine and 1,3‐diamino‐2‐hydroxypropane in a 2:1 molar ratio. The colourless crystals are monoclinic, space group P2 1 /c with cell parameters, a = 10.385(5), b = 11.171(5), c = 17.415(6)Å, β = 93.05(37)° for Z = 8. The asymmetric unit of the structure is composed of two independent molecules of the compound which are in the chair form and adopt the same conformation with equatorial ‐OH and ‐CH 3 groups and axial pyridine substituents. The packing of the molecule seems to be controlled by two independent hydrogen‐bonding sequences.