466
ERKIN et al.
phorus pentoxide in a vacuum dessicator. Compound
IIIa was obtained as hydrochloride.
(1:1) hydrochloric acid from 10% aqueous sodium
hydroxide (in [12], recrystallization from 2-ethoxy-
ethanol was used), washed with cold water, and dried
in a vacuum dessicator over phosphorus pentoxide.
2
-Cyclohexylamino-6-methyl-4(3H)-pyrimidinone
(
IIIb) was prepared in a similar way.
Yield 0.75 g (63%), R 0.88 (B), mp 250 C (decomp.)
f
2
-Benzylamino-6-methyl-4(3H)-pyrimidinone
{mp 254 256 C (decomp.) [12]}.
(
IIIc). Freshly distilled benzylamine, 2.14 g, was
added to 1.56 g of thioether II. The mixture was
heated on an oil bath with stirring at 160 C (bath
temperature) for 5 h and then cooled to room tempera-
ture and diluted with 15 ml of absolute 2-propanol.
Dry hydrogen chloride was passed through the solution
until saturation. The precipitate that formed was
filtered off, recrystallized from 2-propanol, and dried
over phosphorus pentoxide in a vacuum dessicator.
Compound IIIc was obtained as hydrochloride.
ACKNOWLEDGMENTS
The authors express their deep gratitude to
G.V. Erkina for analytical experiments and
A.S. Gavrilov for help in recording the IR spectra.
REFERENCES
1. Wierenga, W., Skulnick, H.I., Stringfellow, D.A.,
Weed, S.D., Renis, H.E., and Eidson, E.E., J. Med.
Chem., 1980, vol. 23, no. 3, p. 237.
. Shimada, A., Iizuka, H., Takada, K., Susuki, S.,
Hirata, M., and Yanagita, T., Jitchuken Zenrinsho
Kenkyuho, 1993, vol. 19, no. 1, p. 35, Chem. Abstr.,
993, vol. 119, 195132 a.
. List, R., Justus Liebigs Ann. Chem., 1886, vol. 236,
no. 1, p. 1.
5
-Bromo-2-butylamino-6-methyl-4(3H)-pyrimi-
dinone (IVa). A mixture of 1.56 g of thioether II and
.46 g of freshly distilled butylamine was heated in a
2
1
sealed ampule at 160 C for 5 h. After cooling, the
ampule was unsealed, and its content was diluted with
1
10 ml of glacial acetic acid. Bromine, 1.6 g, was
3
4
added dropwise with stirring to the resulting solution.
The precipitate that formed was filtered off, washed
with acetic acid, reprecipitated with dilute (1:1)
hydrochloric acid from 10% aqueous sodium hydr-
oxide, washed with cold water, and dried over
phosphorus pentoxide in a vacuum dessicator.
. Wyrzykiewicz, E., Stobieski, M., and Golanki-
ewicz, K., Roczn. Chem., 1977, vol. 51, no. 6,
p. 1227.
5. Brown, D.J., The Pyrimidines, Suppl. I, New York:
Wiley, 1970.
5
-Bromo-2-cyclohexylamino-6-methyl-4(3H)-
6
. Kuliev, F.A., Galstyan, K.A., and Babakhanov, R.A.,
Dokl. Akad. Nauk Azerb. SSR, 1985, vol. 51, no. 6,
p. 27.
pyrimidinone (IVb) was obtained in a similar way.
5
-Bromo-2-benzylamino-6-methyl-4(3H)-pyri-
midinone (IVc). Freshly prepared benzylamine,
.14 g, was added to 1.56 g of thioether II. The mix-
ture was heated on an oil bath with stirring at 160 C
bath temperature) for 5 h. After cooling to 40 C, the
7. Majima, R., Ber., 1908, vol. 41, no. 2, p. 176.
2
8
. Botta, M., De Angelis, F., Finizia, G., Gambacorta, A.,
and Nicoletti, R., Synth. Commun., 1985, vol. 15,
no. 1, p. 27.
(
reaction mixture was diluted with 10 ml of glacial
acetic acid, and, maintaining this temperature, 1.6 g
of bromine was added dropwise with stirring. The
precipitate that formed was filtered off, washed with
acetic acid, reprecipitated with dilute (1:1) hydro-
chloric acid from 10% aqueous sodium hydroxide,
washed with cold water, and dried over phosphorus
pentoxide in a vacuum dessicator.
9
. Akhmerov, M.A., Reznik, V.S., Shagidullin, R.R.,
and Shvetsov, Yu.S., Izv. Akad. Nauk SSSR, Ser.
Khim., 1992, no. 1, p. 169.
1
0. Matsukawa, T. and Shirakawa, K., J. Pharm. Soc. Jpn.,
951, vol. 71, no. 9, p. 943.
1
11. Sen, A.B. and Gupta, S.K., J. Indian Chem. Soc.,
1962, vol. 39, no. 2, p. 129.
1
1
2. Curd, F.H.S., Richardson, D.N., and Rose, F.L.,
5
-Bromo-6-methyl-2-methylthio-4(3H)-pyrimi-
J. Chem. Soc., 1946, no. 5, p. 378.
dinone (V). Bromine, 0.8 g, was added with stirring
at room temperature to a solution of 0.78 g of thio-
ether II in 15 ml of glacial acetic acid. The resulting
suspension was filtered off, the precipitate was
washed with acetic acid, reprecipitated with dilute
3. Roth, B. and Schlomer, L.A., J. Org. Chem., 1963,
vol. 28, no. 10, p. 2659.
14. Simon, I.B. and Kovtunovskaya, I.I., Zh. Obshch.
Khim., 1951, vol. 21, no. 4, p. 760.
RUSSIAN JOURNAL OF GENERAL CHEMISTRY Vol. 73 No. 3 2003