SYNTHESIS OF A 2-HYDRAZINYL-1,6-DIHYDROPYRIMIDINE DERIVATIVE
337
1
3
CH , J = 7.1 Hz), 1.34 t (3H, CH , J = 7.4 Hz), 2.46 s
11.53 br.s (1H, NH), 12.05 br.s (1H, NH). C NMR
3
3
(
7
3H, CH ), 4.06–4.14 m (4H, CH O), 6.1 s (1H, CH),
.25–7.35 m (6H, Ph, OCH=). C NMR spectrum,
spectrum, δ , ppm: 14.1 (CH ), 18.6 (CH ), 19.4
3
2
C
3
3
1
3
(CH ), 25.2 (CH ), 54.1 (CH), 60.9 (CH O), 103.8
3 3 2
5
δ , ppm: 14.2 (CH ), 15.4 (CH ), 22.9 (CH ), 55.1
(
(C ); 127.0 (CH), 129.1 (CH), 129.2 (CH), 141.5 (Ph);
C
3
3
3
2
6
6
2
CH), 60.4 (CH O), 72.2 (CH O), 101.4 (C ), 108 (C );
142.9 (Me C=), 149.1 (C ), 159.7 (C ), 164.6 (5-C=O).
2
2
2
1
1
1
27.9 (CH), 128.5 (CH), 128.6 (CH), 140.7 (Ph);
53.0 (C ), 153.3 (CHOEt), 157.5 (C ) 165.3 (C ),
65.7 (6-C=O). Found, %: C 61.38; H 5.49; N 7.40;
Found, %: C 64.91; H 7.17; N 17.78. C H N O .
Calculated, %: C 64.95; H 7.05; N 17.82.
1
7
22
4
2
7
8a
3
S 8.53. C H N O S. Calculated, %: C 61.27; H 5.41;
FUNDING
1
9
20
2
4
N 7.52; S 8.61.
This study was performed under financial support
by the Ministry of Science and Higher Education of
the Russian Federation in the framework of the base
part of state assignment in the field of research activity
Ethyl 6-methyl-2-oxo-4-phenyl-1,2,3,4-tetrahy-
dropyrimidine-5-carboxylate (6). Hydrazine hydrate,
0
.4 mL (8 mmol), was added with stirring to a solution
of 190 mg (0.6 mmol) of thiazolopyrimidine 5a or
10 mg (0.6 mmol) of 5b in 5 mL of ethanol. The
(
project no. 4.6764.2017/BCh).
2
mixture was refluxed for 3 h and cooled, and the
precipitate was filtered off and washed with ethanol.
Yield 110 mg (70%) from 5a or 96 mg (61%) from 5b,
white crystals, mp 201–202°C; published data [16]:
CONFLICT OF INTERESTS
The authors declare the absence of conflict of
interests.
–
1
mp 202–204°C. IR spectrum, ν, cm : 3246 s (N–H),
117 s (N–H), 2980 m (C–H), 2930 m (C–H), 1726 s
C=O), 1701 s (C=O), 1649 s (C=C), 1223 s (C–O),
092 s (C–O), 758 m (δC–Harom), 698 m (δC–Harom).
3
(
1
REFERENCES
1
. Biginelli, P., Gazz. Chim. Ital., 1893, vol. 23, p. 360.
. Vdovina, S.V. and Mamedov, V.A., Russ. Chem. Rev.,
1
H NMR spectrum, δ, ppm: 1.15 t (3H, CH , J =
3
2
7
.1 Hz), 2.34 s (3H, CH ), 4.01–4.11 m (2H, CH O),
3
2
2
008,
vol.
77,
p.
1017.
doi
10.1070/
5
.40 s (1H, CH), 5.61 s (1H, NH), 7.20–7.35 m (5H,
RC2008v077n12ABEH003894
1
3
Ph), 7.83 s (1H, NH). C NMR spectrum, δ , ppm:
C
3
4
5
. Wan, J.-P. and Liu, Y., Synthesis, 2010, no. 23, p. 3943.
doi 10.1055/s-0030-1258290
1
1
2.8 (CH ), 17.4 (CH ), 54.4 (CH), 58.7 (CH O),
3 3 2
5
00.1 (C ); 125.2 (CH), 126.6 (CH), 127.4 (CH), 142.3
. Sandhu, S.S. and Sandhu, J.S., Arkivoc, 2012, part (i),
p. 66. doi 10.3998/ark.5550190.0013.103
6
2
(
Ph); 144.8 (C ), 151.7 (C ), 164.2 (5-C=O). Found,
: C 64.72; H 6.09; N 10.90. Calculated, %: C 64.60;
H 6.20; N 10.76. C H N O .
%
. Alvim, H.G., Lima, T.B., de Oliveira, A.L., de Oli-
veira, H.C., Silva, F.M., Gozzo, F.C., and Neto, B.A.,
J. Org. Chem., 2014, vol. 79, p. 3383. doi 10.1021/
jo5001498
14
16
2
3
Ethyl 4-methyl-6-phenyl-2-[2-(propan-2-
ylidene)hydrazinyl]-1,6-dihydropyrimidine-5-car-
boxylate (7). A mixture of 180 mg (0.48 mmol) of
thiazolopyrimidine 5c, 4 mL of propan-2-ol, and
6
. Patil, R., Chavan, J., and Beldar, A., World J. Pharm.
Pharm. Sci., 2016, vol. 5, p. 419. doi 10.20959/
wjpps201611-7959
0
3
.3 mL (6.0 mmol) of hydrazine hydrate was stirred for
h at room temperature. The mixture was diluted
7
. Nilsson, B.L. and Overman, L.E., J. Org. Chem., 2006,
vol. 71, p. 7706. doi 10.1021/jo061199m
with 20 mL of water and extracted with ethyl acetate
3×10 mL), the combined extracts were dried over
Na SO and evaporated under reduced pressure, and
8
. Wagman, A.S., Boyce, R.S., Brown, S.P., Fang, E.,
Goff, D., Jansen, J.M., Le, V.P., Levine, B.H., Ng, S.C.,
Ni, Z.-J., Nuss, J.M., Pfister, K.B., Ramurthy, S.,
Renhowe, P.A., Ring, D.B., Shu, W., Subramanian, S.,
Zhou, X.A., Shafer, C.M., Harrison, S.D., John-
son, K.W., and Bussiere, D.E., J. Med. Chem., 2017,
vol. 60, p. 8482. doi 10.1021/acs.jmedchem.7b00922
(
2
4
the oily residue was crystallized from benzene–petro-
leum ether–acetone (30:10:1). Yield 68 mg (44%),
pale pink crystals, mp 147–148°C. IR spectrum, ν,
–
1
cm : 3030 m (NH), 2908 w (C–Haliph), 1681 s (C=O),
1
1
660 m (C=N), 1591 s (C=C
083 s (C–O), 694 s (δC–Harom). H NMR spectrum, δ,
), 1223 s (C–O),
arom
1
9
. Ibrahim, D.A. and El-Metwally, A.M., Eur. J. Med.
Chem., 2010, vol. 45, p. 1158. doi 10.1016/
j.ejmech.2009.12.026
ppm: 1.15 t (3H, CH , J = 7.1 Hz), 1.96 s (3H, CH ),
3
3
2
.11 s (3H, CH ), 2.47 s (3H, CH ), 4.00–4.16 m
3 3
10. El-Mahdy, K.M. and El-Kazak, A.M., Heterocycles,
(
2H, CH O), 5.55 s (1H, CH), 7.20–7.40 m (5H, Ph),
2013, vol. 87, p. 41. doi 10.3987/COM-13-12663
2
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 55 No. 3 2019