4
Tetrahedron Letters
3.
A. G. Waterson, K. L. Stevens, M. J. Reno, Y. -M. Zhang, E. E.
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7.19 (s, 1H); 13C-NMR (75MHz, DMSO,TMS) δ = 161.78, 138.70,
135.03, 133.19, 130.92, 128.85, 126.93, 126.47, 125.52, 125.14;
ESI-MS (m/z): 376 (M+Na)+.
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16. General experimental procedure for the synthesis of pyrimidine
derivatives: β-Cyclodextrin (10 mol %) was dissolved in water (10
mL) by warming to 60–65 oC until a clear solution was formed.
Then, aldehyde (1.0 mmol) was added, after completion of 10
minutes, NH4OAc (2.0 mmol), and 1, 3-diketone (1.0 mmol) added
to the reaction mixture, then the reaction mixture was stirred at 60–
o
65 C until the reaction was complete (as monitored by TLC). After
completion of the reaction, mixture was cooled to room temperature
and β-cyclodextrin was filtered. The aqueous layer was extracted
with ethyl acetate (3 X 10 ml). The combined organic layers were
extracted with water, saturated brine solution and dried over
anhydrous Na2SO4. The combined organic layers were evaporated
under reduced pressure and the resulting crude product was purified
by column chromatography by using ethyl acetate and hexane (3:7)
as eluent. The aqueous layer was cooled to 5 oC to recover β-CD as
indicated in Table 2. The product was confirmed by IR, 1H & 13C
NMR, and mass spectroscopic analysis.
17. Data of representative examples synthesized compounds:
2,4,6-Triphenylpyrimidine (Table 1, Entry 1)1; 1H-NMR (300MHz,
2:1-CDCl3+DMSO,TMS) δ = 8.14 (d, 1H, J = 7.3 Hz), 8.01-7.75 (m,
4H), 7.66-7.46 (m, 9H), 7.33-7.27 (m, 2H); 13C-NMR (75MHz,
DMSO,TMS) δ = 166.91, 143.13, 139.36, 136.77, 135.88, 134.52,
133.10, 131.71, 129.10, 127.48, 124.33; ESI-MS (m/z): 309 (M+H)+.
18. 2-(naphthalen-1-yl)-4,6-diphenylpyrimidine (Table 1, Entry 2); 1H-
NMR (300MHz, 2:1-CDCl3+DMSO,TMS) δ = 8.19-8.09 (m, 3H),
8.02-7.78 (m, 3H), 7.69-7.41 (m, 10H), 7.31-7.26 (m, 2H); 13C-NMR
(75MHz, DMSO,TMS) δ = 164.41, 163.61, 142.41, 141.12, 137.03,
135.36, 134.79, 133.04, 130.95, 129.61, 128.94, 127.46, 127.02,
125.40, 124.32; ESI-MS (m/z): 359 (M+H)+.
19. 2-(anthracen-9-yl)-4,6-diphenylpyrimidine (Table 1, Entry 3); 1H-
NMR (300MHz, 2:1-CDCl3+DMSO,TMS) δ = 8.86 (d, 1H, J = 9.0
Hz), 8.50 (s, 1H), 7.95-7.91 (m, 7H), 7.59-7.41 (m, 10H), 6.78 (s,
1H); 13C-NMR (75MHz, DMSO,TMS) δ = 134.72, 131.99, 128.67,
128.43, 128.15, 127.82, 126.66, 125.88, 124.97, 122.82; ESI-MS
(m/z): 409 (M+H)+.
20. 2-(4-nitrophenyl)-4,6-diphenylpyrimidine (Table 1, Entry 4); 1H-
NMR (300MHz, 2:1-CDCl3+DMSO,TMS) δ = 8.10 (d, 3H, J = 7.0