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16.12.1.8.2.1 Reaction of 3-Cyano-2-methylisothiourea or 2-Cyanoguanidines with Ketones

DOI: 10.1055/sos-SD-116-00063

von Angerer, S.Science of Synthesis Knowledge Updates, (20111222.

Cyclization of 3-cyano-2-methylisothiourea 301 (R1 = SMe) with ketones such as pentan-3-one or acetophenone in the presence of 1,8-diazabicyclo[5.4.0]undec-7-ene gives 2-(methylsulfanyl)pyrimidin-4-amines, but the yields are low.[‌465‌] 2-Cyanoguanidine (301, R1 = NH2) undergoes a similar reaction with various ketones without improvement in the yields.[‌466‌] However, when cyclic ketones such as cyclohexanone or cyclopentanone are used, the yields increase considerably and the reaction becomes useful for the synthesis of cyclocondensed pyrimidin-4-amines 302 (Scheme 169).[‌465‌,‌467‌]

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