714 JOURNAL OF CHEMICAL RESEARCH 2008
72.72; H, 4.58; N, 10.60. Found: C, 72.42; H, 4.58; N, 10.50%. MS
4-(2-Chlorophenyl)-6-phenylpyrimidin-2(1H)-one
(4n): IR (KEr,
(ESI) [M + Na] found (expected): 287.0773 (287.0796).
v, cm-I): 3320, 2849, 1623, 1458, 1349, 772, 690; IH NMR (400
MHz, DMSO-~) 12.04 (hr, s, lH, NH), 8.12-8.29 (m, 4H, ArH),
7.69-7.76 (m, 6H, ArH); BC NMR (100 MHz, DMSO-d6) 8: 156.97,
154.10, 149.20, 149.08, 146.51, 141.71, 138.68, 131.81, 129.07,
4-(4-Bromophenyl)-6-phenylpyrimidin-2(1H)-one
(4g): IR (KEr, v,
cm-I): 3401,2876,1698,754; IHNMR (400 MHz, DMSO-~) 8: 8.16
(d,J= 8.4 Hz, 4H,ArH), 7.77 (d,J= 8.4 Hz, 2H,ArH); 7.56-7.66 (m,
4H,ArH); BCNMR(100MHz,DMSO-~)8:
160.68,134.00,131.98,
127.77,123.21,117.15,69.19,53.86,49.93;
Ca1cd for CIJIllClN20:
131.69, 129.78, 129.02, 127.74, 125.43; Ca1cd for CIJIllBrN20:
C, 58.74; H, 3.39; N, 8.56. Found: C, 58.77; H, 3.69; N, 8.44%. MS
(ESI) [M + H] found (expected): 327.0096 (327.0134).
C, 67.97; H, 3.92; N, 9.91; Found: C, 68.20; H, 4.28; N, 9.60%; MS
(ESI) [M + H] found (expected): 283.0531 (283.0639).
4-(1,2-Dihydro-2-oxo-6-phenylpyrimidine-4-yl)benzonitrile
(4h):
Single crystal X-ray diffraction
IR (KEr, v, cm-I): 3420, 2894, 1620, 1680; IH NMR (400 MHz,
DMSO-~) 8: 12.22 (hr, s, lH, NH), 8.41 (d, J = 8.0 Hz, 2H, ArH),
8.19 (d,J= 6.4 Hz, 2H,ArH), 8.05 (d,J= 8.4 Hz, 2H,ArH), 7.59 (m,
4H,ArH); BCNMR (100 MHz,DMSO-d6) 8:159.70,132.91,129.06,
128.52,127.77,119.63,118.63,117.06,113.71,111.97;
C, 74.71; H, 4.06; N, 15.38. Found: C, 74.71; H, 4.29; N, 15.06%.
The single crystal growth was carried out in EtOH at room temperature.
Crystal data for 4a: empirical formula: CIJI 12N20,colourless, crystal
dimension: 0.32 x 0.19 x 0.16 mm, monoclinic, space group: P2(1)/
c, a
=
13.2000(2) A, b = 7.3243(14) A, c = 13.774(2) A, a = 90",
C17HllN302:
~
=
108.162°, Y = 90°, V = 1265.3(4) A-3, Mr 248.28, Z 4,
=
=
MS (ESI) [M + H] found (expected): 274.0989 (274.0981).
Dc = 1.303 Mg/m-3, A. = 0.71073 A, ,u(Mo Ka) = 0.083 mm-I, F(OOO)
= 520, S = 1.012, RI = 0.0459, WR2= 0.0921, the number of reflections
collected and the number of unique reflections is 6310 and 2234
respectively. Crystallographic data for the structure of 4a reported have
been deposited with the Cambridge Crystallographic Data Centre as
supplementary publication No. CCDC-649143.
4-(2, 3-Dimethoxyphenyl)-6-phenylpyrimidin-2
(1H)-one (41): IR
(KEr, v, cm-I): 3389, 2935, 1662, 1535, 1128, 868, 770; IH NMR
(400 MHz, DMSO-~) 8: 8.00 (d, J = 6.8 Hz, 2H, ArH), 7.75 (d,
J = 5.6 Hz, lH, ArH), 7.56 (m, 4H, ArH), 7.09 (d, J = 8.0 Hz, lH,
ArH), 6.83 (t, lH, ArH), 3.77 (s, 3H, OCH3), 2.46 (s, 3H, OCH3);
BC NMR (100 MHz, DMSO-d6) 8: 149.12, 132.07, 129.12, 127.99,
120.61, 118.03, 115.95, 56.00, 55.97; Ca1cd for CI8HI~203: C,
70.12; H, 5.23; N, 9.09. Found: C, 70.01; H, 5.08; N, 8.89%. MS
(ESI) [M + H] found (expected): 309.1185 (309.1239).
We are grateful to the foundation of the National
Natural Sciences Foundation of China (No. 20772103),
"Natural Sciences Foundation of Jiangsu Province" (No.
BK2007028), and the Surpassing Project in Jiangsu Province
(No.QL200607) for financial support.
4-(3,4-Dimethoxyphenyl)-6-phenylpyrimidin-2(1H)-one
(4j): IR (KEr,
v, em-I):3200, 2835, 1575, 1169, 838, 762; IH NMR (400 MHz,
DMSO-~) 8: 11.95 (hr, s, lH, NH), 8.15 (d, J = 6.4 Hz, 2H, ArH),
7.82 (d,J= 8.4 Hz, lH,ArH), 7.73 (s, lH,ArH), 7.57 (m,4H,ArH),
7.12 (d, J = 8.4 Hz, lH, ArH), 3.88 (d, 6H, OCH3); BC NMR (100
MHz, DMSO-d6) 8: 145.02, 136.07, 128.12, 126.99, 121.61, 117.03,
116.95, 57.00, 55.96; Ca1cd for CI8HI~203: C, 70.12; H, 5.23; N,
9.09. Found: C, 70.01; H, 5.08; N, 8.89%. MS (ESI) [M + H] found
(expected): 309.1338 (309.1240).
Received 15 September 2008; accepted 30 October 2008
Published online: 12 December 2008
4-(2,4-Dichlorophenyl)-6-phenylpyrimidin-2(1H)-one
(4k): IR (KEr,
References
v, em-I): 3420, 2899, 1634, 1498, 828, 778; IH NMR (400 MHz,
DMSO-d6) 8: 12.04 (hr, s, lH, NH), 8.11-8.20 (m, 4H, ArH), 7.49-7.60
(m, 5H, ArH); BC NMR (100 MHz, DMSO-~) 8: 160.20, 144.93,
135.65,132.00, 129.00, 127.05, 117,26; Calcd for CIJIIOC12N20: C,
60.59; H, 3.18; N, 8.83; Found: C, 60.45; H, 3.15; N, 8.59%. MS (ESI)
[M +H] found (expected): 317.0515 (317.0249).
1
2
3
M.M. Paker, F.L. Humaller and D. Mahler, J. Clin. Chem., 1967, 13, 353.
M.A. Lovell, J.D. Robertson, w.J. Teesdale, J.L. Campbell and
4
5
4-(3,4,5- Trimethoxyphenyl)-6-phenylpyrimidin-2(1
H)-one (41): IR
(KEr, v, em-I): 3283,2840, 1634, 1535, 1128, 868, 770; IH NMR
(400 MHz, DMSO-d6) 8: 12.00 (hr, s, lH, NH), 8.12 (d, J= 6.0 Hz,
2H, ArH), 7.53 (m, 6H, ArH), 3.88 (d, 9H, OCH3); BC NMR
(100 MHz, DMSO-d6) 8: 153.27, 140.66, 131.70, 128.97, 127.99,
105.39, 60.36, 56.44; Calcd for CI~18N204: C, 67.44; H, 5.36; N,
8.28. Found: C, 67.41; H, 5.17; N, 8.27%; MS (ESI) [M + H] found
(expected): 339.1448 (339.1345).
6
B. Lagu, D. Tian, G. Chin, D. Nagarathrarn, J. Fang, Q. Shoo, C. Forray,
R.W. Ransom, R.S. L. Chang, K.P. Vyas, K. Zhang and C. Gluchowski,
7
8
9
A.K. Sharma, S. Jayakumar, M.S. Hundal and M.P. Mahajan, J. Chem.
Soc., Perkin Trans.I, 2002,774.
S. Sasaki, N. Cho, Y. Nara, M. Harada, S. Endo, N. Suzuki, S. Furuya and
S. Bartolini, A. Mai, M. Artico, N. Paesano, D. Rotili, C. Spadafora and
4-(4-Nitrophenyl)-6-phenylpyrimidin-2(1H)-one
(4m): IR (KEr, v,
cm-I): 3418,2918, 1681, 1560, 1351,858,758; IH NMR (400 MHz,
DMSO-~) 8: 8.49 (d, J = 8.4 Hz, lH, ArH), 8.39 (d, J = 8.8 Hz,
2H, ArH), 8.20 (d, J = 5.2 Hz, lH, ArH), 7.99 (d, J = 8.4 Hz, lH,
ArH), 7.59 (d,J= 7.2 Hz, 2H,ArH), 7.29 (d,J= 8.4 Hz, lH,ArH),
7.17 (s, lH, ArH), 6.95 (d, J = 9.2 Hz, lH, ArH); BC NMR (100
MHz, DMSO-d6) 8:155.86, 154.02, 143.88, 137.83, 134.53, 131.15,
129.33, 128.80, 128.63, 128.51, 126.76, 126.72, 126.65, 71.11,
50.11; Calcd for C16HllN303: C, 65.53; H, 3.78; N, 14.33. Found:
C, 65.85; H, 3.54; N, 14.40%. MS (ESI) [M + H] found (expected):
294.0828(294.0879).
12 A.R. Khosropour, I. Mohammadpoor-Ba1tork, M.M. Khodaei and
13 F.-A. Kang, J. Kodah, O. Guan, X. Li and W.V. Murray, J. Org. Chem.,