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KATLA et al.
H), 8.28 (1H, s, Ar-H), 7.84 (2H, s, NH2), 7.32-6.94 (m, 4H, Ar-H), 5.24 (2H, t, CH2), 4.82
(1H, s, NH-C=S), 4.46 (2H, t, CH2), 4.32 (1H, s, NH-Ar), 4.12 (2H, s, CH2), 2.12 (1H, d, H-
ipr, J =5.8 Hz), 1.42-1.24 (1H, m, (CH-(CH3)2), 1.14 (6H, d, (CH-(CH3)2, J = 6.4 Hz); 13C-
NMR (300 MHz DMSO-d6, δ/ppm): 172.8 (C20 of C=S), 171.6 (C15 of C=O), 157.2 (C6 of
NH2), 152.4 (C4 of HN-C=O), 147.6, 138.6, 137.4, 127.6, 127.2, 126.8, 126.4, 124.6, 116.8,
69.2, 68.4, 65.4 (C16 of NH), 65.2, 31.2, 18.9, 18.6; MS (m/z): 537 M+.
2-((2-Amino-6-oxo-1H-purin-9(6H)-yl)methoxy)ethyl2-(3-(4-bromophenyl)ureido)-3-
methyl butanoate (3f): Yield: 77%; m.p. 118-120 °C; Anal. Calcd. for C20H24BrN7O5: C,
45.99; H, 4.63; N, 15.30, Found C, 45.86, H, 4.52; N, 15.26; IR (KBr, cm-1); 3432 (N-H),
1
3109 (NH2), 1656 (C=O), 1070 (C-O); H-NMR (300 MHz, DMSO-d6, δ/ppm): 11.2 (1H, s,
N-H), 8.36 (1H, s, Ar-H), 7.62 (2H, s, NH2), 7.46-6.87 (m, 4H, Ar-H), 5.12 (2H, t, CH2), 4.64
(1H, NH-C=S), 4.32 (2H, t, CH2), 4.26 (1H, s, NH-Ar), 4.06 (2H, s, CH2), 2.24 (1H, d, H-ipr,
J = 6.4 Hz), 1.36- 1.24 (1H, m, (CH-(CH3)2), 1.22 (6H, d, (CH-(CH3)2, J = 4.6 Hz); 13C-NMR
(300 MHz, DMSO-d6, δ/ppm): 169.2 (C15 of C=O), 158.4 (C6 of NH2), 151.6 (C4 of HN-
C=O), 148.4 (C20 of C=O), 145.8, 137.5, 136.2, 128.2, 127.9, 127.6, 126.8, 123.8, 118.2, 69.5,
68.4, 66.5 (C16 of NH), 64.8, 30.6, 19.4, 18.8; MS (m/z): 522 M+.
2-((2-Amino-6-oxo-1H-purin-9(6H)-yl)methoxy)ethyl2-(3-(4-fluorophenyl)ureido)-3-
methyl butanoate (3g): Yield: 81%; m.p. 106-108 °C; Anal. Calcd. for C20H24BrN7O5: C,
52.06; H, 5.24; N, 21.25, Found C, 52.01, H, 5.17; N, 21.18; IR (KBr, cm-1): 3440 (N-H),
1
3152 (NH2), 1648 (C=O), 1035 (C-O); H-NMR (300 MHz, DMSO-d6, δ/ppm): 12.4 (1H, s,
N-H), 8.02 (1H, s, Ar-H), 7.92-6.74 (m, 4H, Ar-H), 7.76 (2H, s, NH2), 5.64 (2H, t, CH2), 4.86
(1H, NH-C=S), 4.36 (1H, NH-Ar),) 4.28 (2H, t, CH2), 4.12 (2H, s, CH2), 2.12 (1H, d, H-ipr, J
= 5.6 Hz), 1.82-1.64 (1H, m, (CH-(CH3)2), 1.38 (6H, d, (CH-(CH3)2, J = 6.8); 13C-NMR (300
MHz, DMSO-d6, δ/ppm): 170.4 (C15 of C=O), 157.2 (C6 of NH2), 153.4 (C4 of HN-C=O),
152.6 (C20 of C=O), 146.4, 139.8, 139.4, 127.2, 126.6, 125.8, 125.2, 124.6, 117.5, 68.2, 67.6,
67.2, 65.2, (C16 of NH), 31.6, 19.8, 19.4; MS (m/z) : 461 M+.
2-((2-Amino-6-oxo-1H-purin-9(6H)-yl)methoxy)ethyl2-(3-(3,4-dichlorophenyl)ureido)-3-
methylbutanoate (3h): Yield: 75%; m.p. 102-104 °C; Anal. Calcd. For C20H23Cl2N7O5: C,
46.89; H, 4.52; N, 19.14, Found C, 46.80, H, 4.46; N, 19.10; IR (KBr, cm-1): 3438 (N-H),
1
3112 (NH2), 1652 (C=O), 1074 (C-O); H-NMR (300 MHz, DMSO-d6, δ/ppm): 12.2 (1H, s,
N-H), 8.12 (1H, s, Ar-H), 7.94-6.84 (m, 3H, Ar-H), 7.62 (2H, s, NH2), 5.52 (2H, t, CH2), 4.74
(1H, s, NH-C=S), 4.32 (2H, t, CH2), 4.28 (1H, s, NH-Ar), 4.14 (2H, s, CH2), 2.22 (1H, d, H-
ipr, J = 5.6 Hz), 1.86-1.64 (1H, m, (CH-(CH3)2), 1.26 (6H, d, (CH-(CH3)2, J = 6.2 Hz); 13C-
NMR (300 MHz, DMSO-d6, δ/ppm): 171.5 (C15 of C=O), 158.4 (C6 of NH2), 155.6 (C4 of
C=O), 150.8 (C20 of C=O), 148.2, 138.2, 136.8, 127.4, 126.8, 126.6, 126.2, 125.8, 118.2, 69.2,
67.4, 66.4 (C16 of NH), 62.6, 19.6, 32.4, 19.2; MS (m/z): 512 M+.
2-((2-Amino-6-oxo-1H-purin-9(6H)-yl)methoxy)ethyl2-(3-(3-chloro-4-
fluorophenyl)ureido)-3-methylbutanoate (3i): Yield: 72%; m.p. 100-102 °C; Anal. Calcd. For
C20H23ClFN7O5: C, 48.44; H, 4.67; N, 19.77, Found C, 48.39, H, 4.58; N, 19.72; IR (KBr, cm-
1
1): 3442 (N-H), 3132 (NH2), 1668 (C=O), 1035 (C-O); H-NMR (300 MHz, DMSO-d6,
δ/ppm): 11.9 (1H, s, N-H), 8.24 (1H, s, Ar-H), 7.86-6.92 (m, 3H, Ar-H), 7.74 (2H, s, NH2),
5.42 (2H, t, CH2), 4.62 (1H, s, NH-C=S), 4.46 (2H, t, CH2), 4.16 (1H, s, NH-Ar), 4.24 (2H, s,
CH2), 2.34 (1H, d, H-ipr, J = 5.7 Hz), 1.91-1.74 (1H, (CH-(CH3)2), 1.34 (6H, d, (CH-(CH3)2, J
= 5.2 Hz); 13C-NMR (DMSO-d6, δ/ppm): 172.4 (C15 of C=O), 159.6 (C6 of NH2), 156.2 (C4 of
HN-C=O), 152.6 (C20 of C=O), 149.5, 139.7, 139.2, 128.5, 127.7, 126.8, 126.2, 125.2, 119.4,
69.6, 68.2, 67.6 (C16 of NH ), 63.7, 31.8, 20.2, 19.8; MS (m/z): 496 M+.