Synthesis of 4-methyl-5-arylpyrimidines and 4-arylpyrimidines: route specific markers for the Leuckardt preparation of amphetamine, 4-methoxyamphetamine, and 4-methylthioamphetamine

• Published in: Forensic science international 2001, Vol.115 (1), p.53-67
• Main Authors: Kirkbride, K.Paul, Ward, A.David, Jenkins, Natalie F, Klass, Gunter, Coumbaros, John C
• Format: Article
• Language: English
• Subjects: 4-(4-Methoxybenzyl)pyrimidine; 4-(4-Methylthiobenzyl)pyrimidine; 4-Benzylpyrimidine; 4-Methoxyamphetamine; 4-Methyl-5-(4-methoxyphenyl)pyrimidine; 4-Methyl-5-(4-methylthiophenyl)pyrimidine; 4-Methyl-5-phenylpyrimidine; 4-Methylthioamphetamine; Amphetamine; Amphetamines; Amphetamines - chemistry; Biological and medical sciences; Designer drugs; Ethanol; Fatalities; Forensic medicine; Forensic Medicine - methods; Gas Chromatography-Mass Spectrometry - instrumentation; Gas Chromatography-Mass Spectrometry - methods; Headspace; Humans; Laboratories; Leuckardt reaction; Medical sciences; Public health. Hygiene; Public health. Hygiene-occupational medicine; Pyrimidines; Pyrimidines - chemical synthesis; Pyrimidines - chemistry; Solid phase methods; Solid phase microextraction; Solid phases; Street Drugs - chemistry; Substance Abuse Detection - methods; Tablet computers; Tablets
• ISSN: 0379-0738; 1872-6283
• DOI: 10.1016/S0379-0738(00)00311-X

General synthetic routes to 4-methyl-5-arylpyrimidines and 5-arylpyrimidines are described. 4-Benzylpyrimidine, 4-methyl-5-phenylpyrimidine, 4-(4-methoxybenzyl)pyrimidine, and 4-methyl-5-(4-methoxyphenyl)pyrimidine have been positively identified as route-specific by-products in the Leuckardt preparations of amphetamine and 4-methoxyamphetamine. Using headspace solid phase microextraction (SPME) 4-(4-methoxybenzyl)pyrimidine and 4-methyl-5-(4-methoxyphenyl)pyrimidine have been identified in illicit tablets containing 4-methoxyamphetamine. This is an indication that illicit laboratories use the Leuckardt method for the preparation of 4-methoxyamphetamine. Flatliner tablets containing 4-methylthioamphetamine have been screened for the presence of 4-(4-methylthiobenzyl)pyrimidine and 4-methyl-5-(4-methylthiophenyl)pyrimidine using both headspace and aqueous phase SPME. As these pyrimidines were not detected it would appear likely that illicit laboratories are not using the Leuckardt method for the preparation of 4-methylthioamphetamine.