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Über die Bromierung von substituierten 3,4-Dihydro- und 6-Hydroxy- bzw. 6-Äthoxy-3,4,5,6-tetrahydro-2(1H)-pyrimidinonen

Bromination of 3.4-dihydro- and 6-hydroxy-(6-alkoxy-)-3.4.5.6-tetrahydro-2(1H)-pyrimidinones

Über Heterocyclen, 38. Mitteilung

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Abstract

Bromination of 1-benzyl-4-methyl-3.4-dihydro-2(1H)-pyrimidinone (9 a) with 1 mole Br2 in CHCl3 yields 1-benzyl-5-bromo-6-hydroxy-4-methyltetrahydro-2(1H)-pyrimidinone,12 a, or the 6-ethoxypyrimidinone13 a, according to whether H2O orEtOH is used in working up. With 2 moles Br2,9 a analogously affords the 5.5-dibromopyrimidinnes14 a or15 a. Bromination of the 6-hydroxypyrimidinone10 a yields the same products,12 a and13 a, or14 a and15 a respectively, while the 4-phenyl-pyrimidinones9 b and11 b yield the corresponding 5-bromo-and 5.5-dibromopyrimidinones13 b and15 b. The structures of the compounds12 a-15 b are confirmed by their NMR data and chemical properties: the oxopyrimidinylmethylureas16 a and17 a are formed by the action of methylurea on12 a and13 a, or on14 a and15 a respectively; with hexamethylenetetramine,12 a reacts to give the 5.6-dihydroxypyrimidinone18 a, while13 b is transformed to the 4-phenylpyrimidinone19 b. 13 b was also synthesized from α-bromocinnamaldehyde. The mechanism of bromination is discussed.

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Correspondence to Prof. Dr. G. Zigeuner.

Additional information

Herrn Prof. Dr.O. Hromatka zum 70. Geburtstag gewidmet.

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Zigeuner, G., Schramm, H.W., Fuchsgruber, A. et al. Über die Bromierung von substituierten 3,4-Dihydro- und 6-Hydroxy- bzw. 6-Äthoxy-3,4,5,6-tetrahydro-2(1H)-pyrimidinonen. Monatshefte für Chemie 106, 407–416 (1975). https://doi.org/10.1007/BF01150521

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