Diversity oriented, one-pot, multi-component synthesis of substituted uracil derivatives.
Yogesh Y. Pedgaonkar1, Mariam S. Degani*1, Radhakrishnan. P. Iyer. Iyer2
1
Department of Pharmaceutical Sciences and Technology, Institute of Chemical Technology,
N. Parekh Marg, Matunga, Mumbai - 400019. India.
2
Spring Bank Technologies, Inc.,MA 01757, USA
* Corresponding author. Tel: +91-22-33612213; fax: +91-22-24145614
Email address: ms.degani@ictmumbai.edu.in, m_degani@yahoo.com
Melting points were recorded on Thermomix Compbell electronics, having oil-heating system
and were uncorrected. Analytical thin-layer chromatography (TLC) was carried out on precoated
plates SiO2 (silica gel 60, F 254, Merck). FTIR spectra were recorded on “Buck scientific
infrared spectroscopy M500 spectrophotometer” using KBr pellets. NMR spectra were recorded
on JEOL AL 300 MHz spectrometer or Bruker DMX-400 spectrometer operating at 400 MHz.
Spectra were recorded using DMSO-d6 as solvent; Chemical shifts were represented as  values
using TMS internal standard at  = 0; , proton couplings are indicated as s = singlet, m =
mutiplet. The mass spectrum was recorded on a Waters Q/TOF Micromass spectrometer. All the
reagents and chemicals used were of reagent grade. Elemental analysis was performed with an
ThermoQuest microanalysis apparatus in CHN mode.
Spectral analysis of uracil derivatives
Spectra scans of one compound,5i, have been attached, and data for all others provided. All other
spectra can be scanned and uploaded on request.
1
H NMR of 5i uracil derivative
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C NMR of 5i uracil derivative
Mass spectra of 5i uracil derivative
Spectral analysis of uracil derivatives
5f: M.P. 115-117 ºC; 1H NMR (400 MHz, CDCl3) δ 7.93(1 H, s), δ 7.56 - 7.26 (5H, m), δ 4.023.98( 2 H, t, J= 7.6 Hz), δ 1.64 – 1.61 (2 H, m), δ 1.41 – 1.35 (2 H, m), δ 0.97 – 0.93 (3 H, t, J=
7.6);
C NMR (100 MHz, CDCl3) δ 163.33, 158.85, 149.87, 149.38, 137.92, 129.96, 126.29,
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112.84, 90.52, 42.37, 29.33, 20.10, 13.68.; .; MS (e/z): [M+1] = 270; IR (KBr, Vmax cm-1) 3066,
2956 , 2869 , 2233, 1721 , 1666, 1638, 1593, 1493. Anal. Calcd for C15H15N3O2 (269.12), %: C,
66.90; H, 5.61; N, 15.60..Found, %: C, 67.76; H, 5.86; N, 16.26.
5m :M.P. 103-105 ºC; 1H NMR (400 MHz, CDCl3) δ7.77 (1 H, s), δ 7.59 – 7.06 ( 10 H, m), δ
5.22-5.19 ( 1 H, d, J=14), δ 5.18-5.08 ( 1 H, d, J=14 ),; 13C NMR (100 MHz, CDCl3) δ 158.84,
150.18, 148.98, 135.35, 134.97, 131.94, 131.84, 129.45, 129.22, 128.61, 128.46, 128.26, 128.16,
112.51, 90.83, 45.54.; MS (e/z): [M+1] = 338; IR (KBr Vmax cm-1) 3071, 2936, 2843, 2231,
1736, 1684, 1633, 1513, 1420. Anal. Calcd for C18H12ClN3O2 (337.06), %: C, 64.01; H, 3.58; N,
12.44..Found, %: C, 63.78; H, 3.01; N, 13.27.
5e: M.P. 164-165 ºC; 1H NMR (400 MHz, CDCl3) δ 8.03 (1 H, s), δ 7.53 - 7.25. ( 10 H, m).;
13C NMR (100 MHz, CDCl3) δ 158.85, 150.72, 149.47, 137.77, 133.6, 130.00, 129.62, 129.47,
127.97, 126.28, 112.65, 91.07.; MS (e/z): [M+1] = 290; IR (KBr Vmax cm-1) 3076, 2233, 1728,
1675, 1632, 1591, 1490; Anal. Calcd for C17H11N3O2 (289.09), %: C, 70.58; H, 3.83; N,
14.53..Found, %: C, 71.23; H, 4.38; N, 13.72.
5c: M.P. 216-218 ºC; 1H NMR (300 MHz, CDCl3) δ7.88(1H, s), δ 7.57 - 7.26 (5 H, m), δ 4.87 4.76 (1 H, m), δ 2.43 – 2.30 (2 H, m), δ 1.87 – 1.22 (8 H, m),
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C NMR (100 MHz, CDCl3) δ
159.49, 149.94, 149.27, 138.06, 129.87, 129.83, 126.44, 113.11, 90.57, 55.70, 28.21, 26.13,
25.07.: MS (e/z): [M+1] = 297; IR (KBr Vmax cm-1) 3076, 2920, 2853, 2227, 1740, 1674, 1591,
1493, 1433. Anal. Calcd for C17H17N3O2 (295.13), %: C, 70.58; H, 3.83; N, 14.53.Found, %: C,
71.23; H, 4.38; N, 13.72.
5d : M.P. 172-174 ºC; 1H NMR (400 MHz, CDCl3 & DMSO-d6) δ 8.04 (1 H, s), δ 7.49 – 7.25 (
5 H, m), δ 7.25 – 6.95 ( 4 H, dd), δ 3.81 ( 3 H, s),;
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C NMR (100 MHz, CDCl3) δ 159.99,
159.15, 150.76, 149.71, 137.85, 129.91, 129.87, 129.01, 126.29, 126.07, 114.84, 112.79, 90.90,
55.50.; MS (e/z): [M+1] = 320; IR (KBr Vmax cm-1) 3050, 2926, 2843, 2220, 1731, 1674, 1627 ,
1591, 1425. Anal. Calcd for C18H13N3O3 (319.10), %: C, 67.71; H, 4.10; N, 13.16..Found, %: C,
68.21; H, 4.86; N, 14.03.
5j : M.P. 216-218 ºC ; 1H NMR (300 MHz, CDCl3) δ 8.13 (1 H, s), δ 7.99-7.9 (3 H, m), δ 7.607.30 (8 H, m), δ 2.74 -2.66 (2 H, q, J=7.8 ), δ 1.27-1.2 (3 H, t, J=7.8).; 3C NMR (100 MHz,
CDCl3) δ 160.90, 159.03, 151.42, 149.43, 146.37, 135.30, 134.47, 130.41, 130.20, 129.22,
128.80, 127.56, 126.59, 126.49, 125.99, 125.54, 121.16, 112.88, 90.71, 28.47, 15.32.; MS (e/z):
[M+1] = 368; IR (KBr Vmax cm-1) 3056, 2962, 2233, 1728, 1685, 1635, 1508, 1430, 1050.; Anal.
Calcd for C23H17N3O2 (367.13), %: C, 75.19; H, 4.66; N, 11.44.Found, %: C, 76.37; H, 5.08; N,
10.96.
5k : M.P. 88-89 ºC; 1H NMR (400 MHz, DMSO-d6) δ 9.02 (1 H, s), δ 7.98 – 7.77 ( 4 H, m), δ
7.26 – 7.05 ( 4 H, dd), δ 3.794 ( 3 H, s),; 13C NMR (100 MHz, CDCl3) δ 159.97, 159.18, 153.30,
149.72, 138.85, 131.42, 130.56, 129.90, 129.40, 127.08, 126.00, 124.93, 124.35, 122.26, 114.35,
112.26, 88.73, 55.28 MS (e/z): [M+1] = 372; IR (KBr Vmax cm-1)) 3050, 2926, 2200, 1648, 1627,
1529, 1498, 1420, 1280.; Anal. Calcd for C19H12F3N3O3 (371.09), %: C, 58.92; H, 3.12; N,
10.85.Found, %: C, 59.28; H, 4.19; N, 10.01.