SYNTHESIS OF NEW POLYFUNCTIONAL 5,6,7,8-TETRAHYDROIMIDAZO-...
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Ethyl 7-(4-tert-butylphenyl)-5-oxo-3-[3-(trifluoro-
methyl)phenylamino]-5,6,7,8-tetrahydroimidazo-
[1,5-c]pyrimidine-8-carboxylate (Vj). Yield 58%,
mp 200–201°C. IR spectrum, ν, cm–1: 3230, 3335
[C(CH3)3], 34.17 [C(CH3)3], 43.49 (C8), 55.72 (C7),
61.24 (OCH2), 116.05 (CHarom), 116.84 (CHarom),
117.02 (C8a), 123.21 (C1), 125.40 (CHarom), 125.40
(CHarom), 125.85 (Carom), 127.34 (Carom), 131.11
(CHarom), 133.19 (Carom), 136.34 (Carom), 138.58 (Carom),
144.68 (C3), 150.40 (Carom), 150.45 (C5), 169.27 (C=O).
Found, %: C 65.07; H 6.09; N 11.78. C26H29ClN4O3.
Calculated, %: C 64.93; H 6.08; N 11.65.
1
(N–H); 1735 (C=O, ester); 1710 (C=O). H NMR
spectrum, δ, ppm: 1.20 t (3H, CH2CH3, J = 7.2 Hz),
1.25 s (9H, t-Bu), 4.13 m (2H, OCH2), 4.27 d (1H,
8-H, J = 3.8 Hz), 4.98 m (1H, 7-H), 6.56 s (1H, 1-H),
7.11–7.40 m (5H, Harom), 7.47 t (1H, Harom, J = 7.8 Hz),
7.77 d (1H, Harom, J = 8.5 Hz), 8.32 s (1H, Harom),
8.89 d (1H, NH, J = 2.3 Hz), 9.63 s (1H, NH).
13C NMR spectrum, δC, ppm: 13.69 (CH2CH3), 30.81
[C(CH3)3], 33.98 [C(CH3)3], 43.36 (C8), 55.64 (C7),
61.22 (OCH2), 113.02 (CHarom), 117.14 (CHarom),
117.33 (C8a), 120.95 (CHarom), 123.10 (C1), 124.23 q
(CF3, JCF = 271 Hz), 125.31 (CHarom), 125.79 (CHarom),
129.50 (Carom), 129.74 (CHarom), 136.29 (Carom), 140.19
(Carom), 144.46 (C3), 150.31 (Carom), 150.41 (C5),
169.21 (C=O). Mass spectrum: m/z 501 [M + 1]+.
Found, %: C 62.29; H 5.41; N 11.22. C26H27F3N4O3.
Calculated, %: C 62.39; H 5.44; N 11.19. M 500.52.
REFERENCES
1. Kincl, F.A., Romo, J., Rosenkranz, G., and Sond-
heimer, F., J. Chem. Soc., 1956, p. 4163.
2. Mechoulam, R., Sondheimer, F., Melera, A., and
Kincl, F.A., J. Am. Chem. Soc., 1961, vol. 83, p. 2022.
3. Siddigi, S.M., Melman, N., Olah, M.E., Jain, R.,
Evans, R., Glashofer, M., Radget, W., Cohen, L.A.,
Daly, J.W., Stiles, G.L., and Jacobson, U.A., Nucleosides
Nucleotides, 1996, vol. 15, p. 693.
4. Yoshida, O., Yasukata, T., Sumino, Y., Munekage, T.,
Narukawa, Y., and Nishitani, Y., Bioorg. Med. Chem.
Lett., 2002, vol. 12, p. 3027.
5. Potvin, P.G. and Wong, M.H., J. Chem. Soc., Chem.
Commun., 1987, p. 672.
6. Narayanan, S., Vangapandu, S., and Jain, R., Bioorg.
Med. Chem. Lett., 2001, vol. 11, p. 1133.
Ethyl 7-(4-tert-butylphenyl)-3-(4-methoxyphen-
ylamino)-5-oxo-5,6,7,8-tetrahydroimidazo[1,5-c]py-
rimidine-8-carboxylate (Vk). Yield 30%, mp 168–
170°C. IR spectrum, ν, cm–1: 3335, 3240 (N–H); 1735
(C=O, ester), 1710 (C=O). 1H NMR spectrum, δ, ppm:
1.19 t (3H, CH2CH3, J = 6.9 Hz), 1.25 s (9H, t-Bu),
3.72 s (3H, OCH3), 4.10–4.21 m (3H, OCH2, 8-H),
7. Borchers, A. and Schunack, W., Arch. Pharm., 1984,
vol. 317, p. 455.
8. Collman, J.P., Zhong, M., and Costanzo, S., J. Chem.
Res., Synop., 2001, no. 5, p. 195.
4.95 m (1H, 7-H), 6.45 s (1H, 1-H), 6.83 d (2H, Harom
J = 8.3 Hz), 7.16 d (2H, Harom, J = 8.3 Hz), 7.33 d (2H,
arom, J = 8.0 Hz), 7.61 d (2H, Harom, J = 8.0 Hz),
,
9. Schlögl, K and Woidich, H., Monatsh. Chem., 1956,
vol. 87, p. 679.
H
13
10. Chivikas, C.J. and Hodges, J.C., J. Org. Chem., 1987,
8.76 s and 9.21 s (1H each, NH). C NMR spectrum,
δC, ppm: 13.75 (CH2CH3), 30.85 [C(CH3)3], 34.17
[C(CH3)3], 43.41 (C8), 54.90 (OCH3), 55.55 (C7),
61.22 (OCH2), 114.04 (CHarom), 116.43 (C8a), 118.53
(CHarom), 123.02 (C1), 125.36 (CHarom), 125.77 (Carom),
132.80 (Carom), 136.49 (Carom), 145.51 (C3), 150.37
(Carom), 150.65 (C5), 153.95 (Carom), 169.38 (C=O).
Found, %: C 67.74; H 6.48; N 12.29. C26H30N4O4. Cal-
culated, %: C 67.51; H 6.54; N 12.11.
vol. 52, p. 3591.
11. Wade, J.J., J. Heterocycl. Chem., 1986, vol. 23, p. 981.
12. Kappe, C.O., Tetrahedron, 1993, vol. 49, p. 6937.
13. Dallinger, D., Stadler, A., and Kappe, C.O., Pure Appl.
Chem., 2004, vol. 76, p. 1017.
14. Zigeuner, G., Hamberger, H., Blasche, H., and Sterk, H.,
Monatsh. Chem., 1966, vol. 97, p. 1408.
15. Biginelli, P., Gazz. Chim. Ital., 1893, vol. 23, p. 360.
16. Kappe, C.O., Justus Liebigs Ann. Chem., 1990, p. 505.
Ethyl 7-(4-tert-butylphenyl)-3-(3-chloro-4-meth-
ylphenylamino)-5-oxo-5,6,7,8-tetrahydroimidazo-
[1,5-c]pyrimidine-8-carboxylate (Vl). Yield 41%,
mp 201–202°C. IR spectrum, ν, cm–1: 3335, 3240
(N–H); 1735 (C=O, ester); 1710 (C=O). 1H NMR spec-
trum, δ, ppm: 1.15 t (3H, CH2CH3, J = 6.9 Hz), 1.23 s
(9H, t-Bu), 2.26 s (3H, CH3), 4.15 m (2H, OCH2),
4.36 d (1H, 8-H, J = 3.7 Hz), 5.00 m (1H, 7-H), 6.59 s
(1H, 1-H), 7.09–7.48 m (6H, Harom), 8.09 s (1H, Harom),
17. Molina, P. and Vilaplana, M.J., Synthesis, 1994, no. 12,
p. 1197.
18. Palacios, F., Alouso, C., Aparicio, D., Rubiales, G., and
de los Santoc, J.M., Tetrahedron, 2007, vol. 63, p. 523.
19. Molina, P., Díaz, I., and Tárraga, A., Synlett, 1995,
no. 10, p. 1031.
20. Ding, M.-W., Tu, H.-Y., and Liu, Z.-J., Synth. Commun.,
1997, vol. 27, p. 3657.
21. Palacios, F., Legido, M., Perez de Heredia, I., Rubi-
ales, G., and Ezpeleta, J.M., Heterocycles, 2001, vol. 55,
p. 1641.
13
8.92 s and 9.40 s (1H each, NH). C NMR spectrum,
δC, ppm: 13.85 (CH2CH3), 18.68 (CH3), 30.95
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 45 No. 6 2009