Medicinal Chemistry Research
4-(2-(2-Amino-4-oxo-4,7-dihydro-3H-pyrrolo[2,3-d]
pyrimidin-5-yl)ethyl)-N-(2-(pyridin-2-yl)ethyl)benzamide
(7b)
ethyl-C), 1362 (amine C–N bending), 1435 (H–C–N-
bending), 1531 (NH–C=O amide bending), 1628 (aromatic
C=O symmetric stretching), 3220 (NH-amide stretching)
cm-1. LCMS (ESI) m/z [M+H]+: 436.4 Da. Anal. Calcd.
for C23H22ClN5O2: C, 63.37; H, 5.09; N, 16.07. Found: C,
63.53; H, 5.11; N, 16.23%.
Compound 7b is a pale pink solid. Yield: 88%, m.p. 273–
275 °C.1H NMR (300 MHz, DMSO-d6): δ 2.84–2.86 (m,
2H, CH2 methylene-phenyl), 2.93–3.01(dd, 4H, J1 = 7.2, J2
= 7.8, two CH2 methylene-phenyl and pyridyl), 3.56–3.63
(dd, 2H, J1 = 6.6 Hz, J2 = 6.3 Hz, CH2 methylene-pyridyl),
6.02 (s, 2H, pyrimidine NH2), 6.31 (s, 1H, CH-pyrrole),
7.20–7.28 (m, 4H, para CH-phenyl and CH-pyridyl), 7.68–
7.72 (m, 3H, CH-pyridyl), 8.48–8.5 (m, 2H, para CH-
phenyl), 10.17 (s, 1H, NH-pyrrole), 10.61 (s, 1H, pyr-
imidine NH-sec. amide) ppm. 13C NMR (100 MHz,
DMSO-d6): δ 166.6 (amide C=O), 159.8 (amide C=O),
159.7 (pyrimidine-C), 152.7 (pyrimidine-C), 151.8 (pyr-
idyl-C), 149.5 (pyrrole-C), 146.2 (pyrrole-C), 136.8 (pyr-
idyl-C), 132.4 (phenyl-C), 128.6 (phenyl-C), 127.4 (phenyl-
C), 123.5 (phenyl-C), 121.9 (phenyl-C), 118.1 (pyrrole-C),
113.8 (pyrrole-C), 99.2 (pyrrole-C), 37.8 (pyridyl ethyl-C),
36.6 (phenyl methylene-C), 36.5 (pyridyl methylene-C),
28.4 ppm. FT-IR υ 775 (pyridyl C–H), 841 (para-sub-
stituted phenyl C–H), 1289 (phenyl ethyl-C), 1341 (amine
C–N bending), 1433 (H–C–N-bending), 1534 (NH–C=O
amide bending), 1632 (aromatic C=O symmetric stretch-
ing), 3235 (NH-amide stretching) cm-1. LCMS (ESI) m/z
[M+H]+: 403.3 Da. Anal. Calcd. for C22H22N6O2: C,
65.66; H, 5.51; N, 20.88. Found: C, 65.82; H, 5.48; N,
20.92%.
4-(2-(2-Amino-4-oxo-4,7-dihydro-3H-pyrrolo[2,3-d]
pyrimidin-5-yl)ethyl)-N-(2-(piperidin-1-yl)ethyl)benzamide
(7d).
Compound 7d is a pale pink solid. Yield: 84%, m.p. 232–
235 °C.1H NMR (300 MHz, DMSO-d6) δ 1.37–1.38 (m,
2H, CH2 piperidyl methylene), 1.47–1.48 (m, 4H, CH2
piperidyl methylene), 2.37–2.43 (m, 6H, CH2 piperidyl
methylene and CH2 aliphatic methylene), 2.82–2.86 (m, 2H,
CH2 methylene-phenyl), 2.94–2.96 (m, 2H, CH2 methy-
lene-phenyl), 3.3 (m, 2H, CH2 aliphatic methylene), 5.99 (s,
2H, pyrimidine NH2), 6.31 (s, 1H, pyrrole CH), 7.25–7.28
(d, 2H, J = 7.5 Hz, para phenyl CH), 7.71–7.73 (d, 2H, J =
7.8 Hz, para phenyl CH), 8.27 (m, 1H, 1o amide NH), 10.14
(s, 1H, NH-pyrrole), 10.61 (s, 1H, pyrimidine NH-sec.
amide) ppm. 13C NMR (100 MHz, DMSO-d6) δ 24.5
(phenyl ethyl-C), 26.0 (phenyl ethyl-C), 28.4 (piperidyl
ethyl-C), 36.5 (piperidyl ethyl-C), 37.3 (piperidyl-C), 54.5
(piperidyl-C), 58.2 (piperidyl-C), 99.2 (pyrrole-C), 113.8
(pyrrole-C), 118.1 (phenyl-C), 127.4 (phenyl para-C),
128.6 (phenyl para-C), 132.5 (phenyl-C), 146.2 (pyrrole-
C), 151.7 (pyrimidine-C), 152.6 (pyrimidine-C), 159.7
(amide C=O), 166.5 (amide C=O) ppm. FT-IR υ, 844
(para-substituted phenyl C–H bending), 1362 (amine C–N
bending), 1436 (H–C–N-bending), 1532 (NH–C=O amide
bending), 1633 (aromatic C=O symmetric stretching), 3221
(NH-amide stretching) cm−1. LCMS (ESI) m/z [M+H]+:
409.3 Da. Anal. Calcd. for C22H28N6O2: C, 64.68; H, 6.91;
N, 20.57. Found: C, 64.85; H, 6.88; N, 20.69%.
4-(2-(2-Amino-4-oxo-4,7-dihydro-3H-pyrrolo[2,3-d]
pyrimidin-5-yl)ethyl)-N-(4-chlorophenethyl)benzamide (7c).
Compound 7c is a pale orange solid. Yield: 92%, m.p. 278–
281 °C.1H NMR (300 MHz, DMSO-d6) δ 2.83-2.85 (m,
4H, two CH2 methylene-phenyl), 2.93–2.96 (m, 2H, CH2
methylene -4-Cl phenyl), 3.42–3.47 (m, 2H, CH2
methylene-4-Cl phenyl), 6.0 (s, 2H, pyrimidine NH2), 6.31
(s, 1H, CH-pyrrole), 7.25–7.27 (m, 4H, para CH-4-Cl
phenyl), 7.33–7.36 (d, 2H, J = 8.4 Hz, para CH-phenyl),
7.69–7.72 (d, 2H, J = 7.8 Hz, para CH-phenyl), 8.45–8.46
(m, 1H, 1o amide NH), 10.14 (bs, 1H, NH-pyrrole), 10.61
(s, 1H, pyrimidine NH-sec. amide) ppm. 13C NMR (100
MHz, DMSO-d6) δ 28.4 (phenyl ethyl-C), 34.8 (4-Cl phe-
nyl ethyl-C), 36.5 (phenyl ethyl-C), 36.7 (4-Cl phenyl
methyl-C), 99.2 (pyrrole-C), 113.8 (pyrrole-C), 118.1
(pyrrole-C), 127.4 (phenyl-C), 128.6 (phenyl para-C),
128.6 (phenyl para-C), 131.0 (4-Cl phenyl para-C), 131.1
(4-Cl phenyl para-C), 132.4 (4-Cl phenyl-C), 139.1 (pyr-
role-C), 146.2 (pyrrole-C), 151.8 (pyrimidine-C), 152.6
(pyrimidine-C), 159.7 (amide C=O), 166.6 (amide C=O)
ppm. FT-IR υ 775 (para-substituted phenyl C–H bending),
841 (para-substituted phenyl C–H bending), 1286 (phenyl
4-(2-(2-Amino-4-oxo-4,7-dihydro-3H-pyrrolo[2,3-d]
pyrimidin-5-yl)ethyl)-N-(4-fluorophenethyl)benzamide (7e).
Compound 7e is an off-white solid. Yield: 71%, m.p. 275–
278 °C. 1H NMR (300 MHz, DMSO-d6, δ ppm, 2.80–2.85
(m, 4H, two CH2 methylene-phenyl), 2.93–2.96 (m, 2H,
CH2 methylene-4-F phenyl), 3.42–3.48 (m, 2H, CH2
methylene-4-F phenyl), 6.0 (s, 2H, pyrimidine NH2), 6.32
(s, 1H, CH-pyrrole), 7.08–7.14 (t, 2H, J = 9.0 Hz, para CH-
4-Fluorophenyl), 7.25–7.28 (d, 4H, J = 7.8 Hz, para CH-4-
Fluorophenyl and para phenyl CH), 7.69–7.72 (d, 2H, J =
7.8 Hz, para phenyl CH), 8.43–8.45 (m, 1H, 1o amide
NH),10.14 (bs, 1H, NH-pyrrole), 10.62 (s,1H, pyrimidine
NH-sec. amide), 13C NMR (300 MHz, DMSO-d6, δ ppm)
28.4 (phenyl ethyl-C), 34.6 (4-Fluorophenyl-C), 36.5 (4-
Fluorophenyl-C), 99.2 (pyrrole-C), 113.8 (pyrrole-C),