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Synthesis of 1,3,5,5–tetranitrohexahydropyrimidine–2,2,4,4,6,6–d 6 (DNNC–d 6 ) and its adiol–d 4 precursor using paraformaldehyde–d 2 and unlabeled reaction ingredients
Author(s) -
Shackelford Scott A.
Publication year - 1991
Publication title -
journal of labelled compounds and radiopharmaceuticals
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.432
H-Index - 47
eISSN - 1099-1344
pISSN - 0362-4803
DOI - 10.1002/jlcr.2580291104
Subject(s) - paraformaldehyde , chemistry , anhydrous , nitration , yield (engineering) , methanol , aqueous solution , nuclear chemistry , medicinal chemistry , organic chemistry , metallurgy , materials science
Using commercially available paraformaldehyde–d 2 , the subject compounds were synthesized with unlabeled reactants and ordinary solvents. The 2,2–dinitropropane–1,3‐diol–1,1,3,3–d 4 (ADIOL–d 4 ) precursor was produced in greater than 99% isotopic purity with aqueous depolymerized paraformaldehyde–d 2 and CH 3 NO 2 in alkaline solution followed by oxidative AgNO 3 /NaNO 2 nitration; then, ADIOL–d 4 and depolymerized paraformaldehyde–d 2 with t ‐butylamine in methanol afforded cyclic 1,3–di– t ‐butyl–5,5–dinitrohexahydropyrimidine–2,2,4,4,6,6–d δ (DBNP–d 6 ). The 97% isotopically pure DNNC–d 6 product resulted in 71% yield from an anhydrous HNO 3 nitration of DBNP–d 6 .