FEATURES OF THE SYNTHESIS OF S-MONOBENZYL
1243
sodium hydroxide and 2 g (14 mmol) of 6-methyl-2-
thiouracil. To the solution was added 6 ml of dioxane and
then dropwise a solution of 1.77 g (14 mmol) of benzyl
chloride in 5 ml of dioxane. The mixture was stirred for
1 h at 50°C. On cooling the separated precipitate was
filtered off, washed with cold water, dried, and recrystal-
lized from benzene.Yield of colorless crystalline compound
II 3.93 g (96%), mp 173–174°C (publ: mp 172–173°C
[1]), Rf 0.62. 1H NMR spectrum, δ, ppm: 2.2 s (3H, CH3),
4.3 s (2H, SCH2), 5.95 s (1H, H5), 7.05–739 m (5H, Ar–
H), 1.2 C (1H, NH).
in a vacuum, the residue was washed with cold water
and recrystallized from benzene. Yield of colorless
crystalline compound IV 3.61 g (90%), mp 59–60°C, Rf
0.73. 1H NMR spectrum, δ, ppm: 1.8 s (3H, CH3), 4.25 s
(2H, SCH2), 5.5 s (1H, H5), 7.2–7.7 m (10H, Ar–H).
6-Methyl-2-(m-phenoxybenzylthio)-3-(m-phen-
oxybenzyloxy)pyrimidine (V) was obtained by the same
procedure.. Yield 83%, colorless crystalline substance,
mp 78–79°C, Rf 0.75. 1H NMR spectrum, δ, ppm: 2.0 s
(3H, CH3), 4.3 s ( 2H, SCH2), 5.8 s (1H, H5), 6.20–
7.45 m (18H, Ar–H).
1H NMR spectra of compounds in DMSO-d6 were
registered on spectrometer Varian at operating frequency
300 MHz, internal reference HMDS. The homogeneity
of compounds obtained was proved by TLC on Silufol
UV-254 plates, eluent ethyl ether–ethanol (1:0.05 by
volume), development in iodine vapor. Melting points were
measured by melting compounds in capillaries.
4-Hydroxy-6-methyl-2-(m-phenoxybenzylthio)-
pyrimidine (III) was obtained by the same procedure.
Yield 94%, colorless crystalline substance, mp 137–
1
139°C, Rf 0.64. H NMR spectrum, δ, ppm: 2.0 s (3H,
CH3), 4.25 s (2H, SCH2), 5.95 s (1H, H5), 6.75–7.40 m
(9H, Ar–H), 12.2 s (1H, NH).
3-Benzyloxy-2-benzylthio-6-methylpyrimidine
(IV). In 6 ml of water was dissolved 1.12 g (28 mmol) of
sodium hydroxide and 2 g of 6-methyl-2-thiouracil. To
the solution was added 6 ml of dioxane and then dropwise
a solution of 3.54 g (28 mmol) of benzyl chloride. The
mixture was stirred for 3 h at 50°C. On cooling the
reaction mixture was filtered, the filtrate was evaporated
REFERENCES
1. Nugent, Richard,A., US Patent 5981537, 1994; Ref. Zh. Khim.,
2001, 19O.112.
2. Popov, Yu.V., Korchagina, T.K., and Stepochkina, D.G., Zh.
Org. Khim., 2001, vol. 37, p. 783.
RUSSIAN JOURNALOF ORGANIC CHEMISTRY Vol. 41 No. 8 2005