Microwave-Expedited One-Pot Synthesis of Pyrimidines
123
4-(3-Bromophenyl)-6-phenyl-(1H)-pyrimidin-2-one 3f
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mp 196–200◦C. (Found: C 62.49, H 3.68, N 4.35. C16H11N2OBr
requires C 62.60, H 3.71, N 4.29%.) δH (CDCl3, 300 MHz) 8.24
(br s, 1H), 8.10–8.02 (m, 3H), 7.69 (d, 1H, J 8.1), 7.60–7.59 (m,
3H), 7.42 (t, 1H, J 7.8), 7.10 (s, 1H). νmax(KBr)/cm−1 3434,
2923, 1672, 1639, 1632, 1413, 1383, 763, 589. m/z (HRMS-
FAB) 348.9967, C16H11N2OBr (M + Na)+ requires 348.9952.
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4-(3-Bromophenyl)-6-phenylpyrimidin-2-ylcyanamide 3h
mp 238–40◦C. (Found: C 62.88, H 3.97, N 8.67. C16H11N2OBr
requires C 62.79, H 4.03, N 8.61%.) δH ([D6]DMSO,
400 MHz) 8.54 (s, 1H), 8.40–37 (m, 3H), 8.22 (s, 1H),
7.75 (d, 1H, J 8.5), 7.57–7.50 (m, 4H), 6.43 (br s, 1H).
νmax(KBr)/cm−1 3320, 3145, 2922, 2852, 2180, 1579, 1566,
1421, 1337, 768, 583. m/z (ESI) 127(37), 155(48), 163.9(30),
171(50), 199.1(54), 209.1(33), 211.1(45), 227.4(35), 252.7(45),
255(100), 269.1(22), 281.2(67), 283(65), 293.4(17), 311.2(15),
325.1(12), 339.9(10), 351(M+, 8), 353(M+ + 2, 6), 371.3(10),
435.3(20).
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1,3-Diphenylpropan-1-one 8
mp 68–70◦C (lit. 71–72◦C[16]). (Found: C 85.61, H 6.75.
C15H14O requires C 85.68, H 6.71%.) δH (CDCl3, 300 MHz)
7.96 (d, 2H, J 7.2), 7.56 (t, 2H, J 7.3), 7.45 (t, 2H, J 7.5),
7.33–7.19 (m, 4H), 3.31 (t, 2H, J 7.7), 3.07 (t, 2H, J 7.6).
νmax(KBr)/cm−1 2922, 1681, 1448, 1364, 1292, 1208, 743, 701.
[9] For recent reviews on the synthesis of heterocyclic compounds under
microwave irradiation, see:
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JA01205A031
Acknowledgments
We acknowledge the Department of Science and Technology (DST) and the
Council of Scientific and Industrial Research (CSIR), Government of India,
for financial support. S.J. thanks CSIR for a research fellowship.
(b) F. G. Badder, F. H.Al-Hajjar, N. R. El-Rayyes, J. Heterocycl. Chem.
1976, 13, 257.
(c) For leading references on the discussion of properties and synthesis
of pyrimidines, see: D. J. Brown,The Pyrimidines, Supplement-1 1962
(Wiley: NewYork, NY); D. J. Brown, The Pyrimidines, Supplement-2
1970 (Wiley: New York, NY).
(d) V. G. Vodopyanov, V. G. Golov, Yu. I. Dergunov, M. G. Ivanov,
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