ChemInform Abstract: Unusual Ring Closure Reaction of Amides with Pyrimidines: Novel Stereoselective Synthesis of Hexahydroimidazo[1,2‐c]pyrimidines.

Abstract

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2‐Sulfonyliminodihydropyrimidines: A Novel Class of Analgesic Compounds

“…The pyrimidine derivatives 6 were prepared according to the literature procedure [13]. Reaction of 2-sulfonylaminopyrimidines 4A, B with the appropriate iodocarboxamide 5a -g in the presence of Hünig's base in DMF provided the corresponding 2-tosylimino-1-substituted dihydropyrimidines 6Aa -g and 2-mesyliminodihydropyrimidines 6Bd, e. In some cases, pyrimidines 7 were obtained along with dihydropyrimidines 6 (Scheme 2).…”

“…Yield 90%; m.p. : 208 -2108C (lit [13] 204 -2068C). General procedure for the synthesis of iodoacetamides 5d -f [19] Powdered KI (5 mmol) was added to a solution of the corresponding chlorocarboxamide (1 mmol) in dry acetone (1 mL).…”

“…HRMS were obtained using a VG Autospec TRIO 1000 instrument (Fisons, Manchester, UK). The ionization mode used in mass spectra was electron impact were prepared as described in the literature [13].…”