O,O-DIALKYL 1-((4,6-DICHLOROPYRIMIDIN-2-YL)CARBAMYLOXY)ALKYLPHOSPHONATES 817
O,O-Dimethyl 1-((4,6-dichloropyrimidin-2-yl)carbamyloxy)-1-(4-nitroph
1
enyl) methylphosphonates (6i). White solid: H-NMR (CDCl3, 200 MHz): δ =
3.86 (d, 6H, 2OCH3, J = 11.0 Hz), 6.23 (d, 1H, OCHP, J = 15.2 Hz), 7.30–7.55 (m,
5H, Ar–H), 9.90 (s, 1H, NH); 31P-NMR (CDCl3, 81 MHz): δ = 18.5; IR (υ/cm−1): 3426
(N H), 3041 (Ar–H), 1764 (C O), 1608, 1581, 1554 (C C), 1216 (P O), 1184 (C O),
1040 (P O C); Anal. Calcd. for C14H13Cl2N4O7P: C, 37.25; H, 2.88; N, 12.41. Found:
C, 37.12; H, 2.94; N, 12.08.
O,O-Diethyl 1-((4,6-dichloropyrimidin-2-yl)carbamyloxy)ethylphosphon
ates (6j). White solid: 1H-NMR (CDCl3, 200 MHz): δ = 1.65 (m, 3H, CH3), 1.44–1.48
(m, 6H, 2CH3), 4.27–4.30 (m, 4H, 2OCH2), 5.43–5.45 (m, 1H, OCHP), 7.06 (s, 1H, Ar–H),
10.23 (s, 1H, NH); 31P-NMR (CDCl3, 81 MHz): δ = 21.5; IR (υ/cm−1): 3350 (N H), 3010
(Ar–H), 1767 (C O), 1612, 1580, 1556 (C C), 1216 (P O), 1182 (C-O), 1050 (P O C);
Anal. Calcd. for C11H16Cl2N3O5P: C, 35.48; H, 4.30; N, 11.29. Found: C, 35.41; H, 4.34;
N, 10.81.
O,O-Diethyl 1-((4,6-dichloropyrimidin-2-yl)carbamyloxy)-1-(phenyl)met
hylphosphonates (6k). White solid: 1H-NMR (CDCl3, 200 MHz): δ = 1.15–1.17 (m,
6H, 2CH3), 4.15–4.17 (m, 4H, 2OCH2), 6.18 (d, 1H, OCHP, J = 15.2 Hz), 7.38–7.61 (m,
6H, Ar–H), 9.80 (s, 1H, NH); 31P-NMR (CDCl3, 81 MHz): δ = 18.1; IR (υ/cm−1): 3416
(N H), 3026 (Ar–H), 1774 (C O), 1577, 1555, 1508 (C C), 1216 (P O), 1172 (C O),
1047 (P O C); Anal. Calcd. for C16H18Cl2N3O5P: C, 44.23; H, 4.14; N, 9.67. Found: C,
44.36; H, 4.17; N, 9.56.
O,O-Diethyl 1-((4,6-dichloropyrimidin-2-yl)carbamyloxy)-1-(2-chlorophe
1
nyl)methylphosphonates (6l). White solid: H-NMR (CDCl3, 200 MHz): δ = δ =
1.15–1.19 (m, 6H, 2CH3), 4.15–4.17 (m, 4H, 2OCH2), 5.60 (d, 1H, OCHP, J = 14.2 Hz),
7.22–7.78 (m, 5H, Ar–H), 9.40 (s, 1H, NH); 31P NMR (CDCl3, 81 MHz): δ = 21.2; IR
(υ/cm−1): 3422 (N H), 3030 (Ar–H), 1772 (C O), 1577, 1551, 1476 (C C), 1216 (P O),
1177 (C O), 1051 (P O C); Anal. Calcd. for C16H17Cl3N3O5P: C, 41.02; H, 3.62; N,
9.09. Found: C, 40.82; H, 3.58; N, 8.57.
O,O-Diethyl 1-((4,6-dichloropyrimidin-2-yl)carbamyloxy)-1-(4-chlorophe
1
nyl)methylphosphonates (6m). White solid: H-NMR (CDCl3, 200 MHz): δ =
1.18–1.21 (m, 6H, 2CH3), 4.24–4.28 (m, 4H, 2OCH2), 6.14 (d, 1H, OCHP, J = 14.2 Hz),
7.28–7.57 (m, 5H, Ar–H), 9.90 (s, 1H, NH); 31P-NMR (CDCl3, 81 MHz): δ = 17.0; IR
(υ/cm−1): 3321 (N H), 3029 (Ar–H), 1781 (C O), 1575, 1552, 1509 (C C), 1216 (P O),
1165 (C O), 1051 (P O C); Anal. Calcd. for C16H17Cl3N3O5P: C, 41.02; H, 3.62; N,
9.09. Found: C, 41.07; H, 3.67; N, 8.54.
O,O-Diisopropyl 1-((4,6-dichloropyrimidin-2-yl)carbamyloxy)ethylphosp
honates (6n). White solid: 1H-NMR (CDCl3, 200 MHz): δ = 1.06–1.65 (m, 15H, 5CH3),
4.80–4.87 (m, 2H, 2CH), 5.18–5.21 (m, 1H, OCHP), 7.30 (s, 1H, Ar–H), 9.70 (s, 1H, NH);
31P-NMR (CDCl3, 81 MHz): δ = 19.4; IR (υ/cm−1): 3310 (N H), 3022 (Ar–H), 1768
(C O), 1576, 1546, 1507 (C C), 1212 (P O), 1180 (C O), 1039 (P O C); Anal.
Calcd. for C13H20Cl2N3O5P: C, 39.02; H, 5.02; N, 10.50. Found: C, 39.07; H, 4.87; N,
10.33.
O,O-Diisopropyl 1-((4,6-dichloropyrimidin-2-yl)carbamyloxy)-1-(phenyl)
methylphosphonates (6o). White solid: 1H-NMR (CDCl3, 200 MHz): δ = 1.31–1.41
(m, 12H, 4CH3), 4.78–4.98 (m, 2H, 2CH), 6.11 (d, 1H, OCHP, J = 14.2 Hz), 7.27–7.64 (m,
6H, Ar–H), 10.10 (s, 1H, NH); 31P NMR (CDCl3, 81 MHz): δ = 15.7; IR (υ/cm−1): 3426
(N H), 3026 (Ar–H), 1772 (C O), 1576, 1553, 1455 (C C), 1217 (P O), 1172 (C O),