Molecules 2021, 26, 1952
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134.0, 131.9, 131.3, 126.9, 114.7, 102.6, 66.6, 36.1, 28.4. M.F. C15H14ClN5O3; M. Wt. Cal: 347;
Found: ESI-Ms m/z, 348 [M + H]+. Elemental analysis: Cal: C, 51.81; H, 4.06; N, 20.14;
Found: C, 51.79; H, 4.01; N, 20.10.
1-((1-Benzyl-1H-1,2,3-triazol-4-yl)methyl)-6-chloro-3-methylpyrimidine-2,4(1H,3H)-dione (5f):
Light yellow solid; 92% yield; M.P. 115–118 ◦C; 1H-NMR (400 MHz, CDCl3),
δ, ppm: 8.59
(dd, J = 7.3, 0.9 Hz, 1H), 8.24 (dd, J = 8.3, 0.9 Hz, 2H), 7.81–7.72 (m, 2H), 6.91 (d, J = 8.7 Hz,
1H), 5.98 (s, 1H), 4.85 (d, J = 2.5 Hz, 2H), 4.43 (s, 2H), 3.35 (s, 3H). 13C-NMR (100.6 MHz,
CDCl3), δ, ppm: 190.8, 164.3, 160.5, 144.7, 134.0, 131.9, 131.3, 126.9, 114.7, 102.6, 73.3, 36.1,
28.4. M.F. C15H14ClN5O2; M. Wt. Cal: 331; Found: ESI-Ms m/z, 332 [M + H]+. Elemental
analysis: Cal: C, 54.30; H, 4.25; N, 21.11; Found: C, 54.36; H, 4.30; N, 21.18.
1-((1-(4-Bromobenzyl)-1H-1,2,3-triazol-4-yl)methyl)-6-chloro-3-methylpyrimidine-2,4(1H,3H)-
dione (5g): Pale green; 81% yield; M.P. 138–140 ◦C; 1H-NMR (400 MHz, CDCl3),
δ
, ppm:
7.58 (s, 1H), 7.51 (dd, J = 8.5, 2.4 Hz, 2H), 7.18 (dd, J = 15.3, 8.4 Hz, 2H), 5.93 (s, 1H), 5.46
(s, 2H), 5.32 (s, 2H), 3.30 (s, 3H). 13C-NMR (100.6 MHz, CDCl3),
, ppm: 160.6, 151.0, 145.3,
δ
142.5, 134.4, 132.3, 131.9, 129.8, 123.3, 102.3, 53.5, 41.9, 28.3. M.F. C15H13ClBrN5O2; M. Wt.
Cal: 409; Found: ESI-Ms m/z, 410 [M + H]+. Elemental analysis: Cal: C, 43.87; H, 3.19; N,
17.05; Found: C, 43.80; H, 3.15; N, 17.01.
6-Chloro-3-methyl-1-((1-(4-methylbenzyl)-1H-1,2,3-triazol-4-yl)methyl)pyrimidine-2,4(1H,3H)-
◦
dione (5h): Off white solid; 78% yield; M.P. 110–112 C; 1H-NMR (400 MHz, CDCl3),
δ,
ppm: 7.53 (s, 1H), 7.18 (d, J = 7.2 Hz, 4H), 5.93 (s, 1H), 5.46 (s, 2H), 5.31 (s, 2H), 3.30 (s, 3H),
2.35 (s, 3H). 13C-NMR (100.6 MHz, CDCl3),
δ, ppm: 160.7, 151.0, 145.4, 138.8, 131.2, 130.5,
129.8, 129.5, 128.5, 128.2, 102.3, 54.1, 41.9, 28.3, 21.1. M.F. C16H16ClN5O2; M. Wt. Cal: 345.
Elemental analysis: Cal: C, 55.58; H, 4.66; N, 20.25; Found: C, 55.50; H, 4.60; N, 20.20.
6-Chloro-1-((1-(3-methoxybenzyl)-1H-1,2,3-triazol-4-yl)methyl)-3-methylpyrimidine-2,4(1H,3H)-
dione (5i): Light yellow solid; 80% yield; M.P. 98–100 ◦C; 1H-NMR (400 MHz, CDCl3),
δ,
ppm: 7.57 (s, 1H), 7.29 (m, 2H, J = 7.2 Hz), 6.86 (m, 2H, J = 7.1 Hz), 5.93 (s, 1H), 5.46 (s, 2H),
5.32 (s, 2H), 3.81 (d, J = 2.4 Hz, 3H), 3.30 (s, 3H). 13C-NMR (100.6 MHz, CDCl3),
δ
, ppm:
190.8, 164.3, 160.5, 144.7, 134.0, 131.9, 131.3, 126.9, 114.7, 102.6, 73.3, 66.6, 37.7, 36.1, 35.2,
28.4. M.F. C16H16ClN5O3; M. Wt. Cal: 361. Elemental analysis: Cal: C, 53.12; H, 4.46; N,
19.36; Found: C, 53.08; H, 4.40; N, 19.30.
6-Chloro-3-methyl-1-((1-(3-phenoxybenzyl)-1H-1,2,3-triazol-4-yl)methyl)pyrimidine-2,4(1H,3H)-
dione (5j): Cream yellow solid; 86% yield; M.P. 101–105 ◦C; 1H-NMR (400 MHz,
CDCl3 + DMSO), δ, ppm: 8.57 (d, J = 7.3 Hz, 2H), 8.43 (d, J = 8.2 Hz, 2H), 8.07 (s, 1H),
7.86 (t, J = 7.8 Hz, 2H), 7.46 (d, J = 8.9 Hz, 2H), 7.06 (d, J = 8.9 Hz, 2H), 4.84 (s, 4H), 3.34
(s, 3H). M.F. C21H18ClN5O3; M. Wt. Cal: 423; Found: ESI-Ms m/z, 424 [M + H]+. Elemental
analysis: Cal: C, 59.51; H, 4.28; N, 16.52; Found: C, 59.50; H, 4.21; N, 16.45.
1-((1-((3-(2H-Chromen-3-yl)-1,2,4-oxadiazol-5-yl)methyl)-1H-1,2,3-triazol-4-yl)methyl)-6-
chloro-3-methylpyrimidine-2,4(1H,3H)-dione (5k): Off white solid; 86% yield; M.P. 125–128 ◦C
;
1H-NMR (400 MHz, CDCl3),
7.16–6.93 (t, J = 7.5 Hz, 2H), 6.89 (d, 2H, J = 8.2 Hz), 5.97 (s, 1H), 5.84 (s, 2H), 5.40 (s, 2H),
5.16 (s, 2H), 3.32 (s, 3H). 13C-NMR (100.6 MHz, CDCl3),
, ppm: 171.4, 166.2, 160.6, 154.6,
δ, ppm: 7.97 (s, 1H), 7.44 (s, 1H), 7.25 (d, 1H, J = 5.7 Hz),
δ
151.1, 145.2, 143.0, 131.4, 129.5, 128.4, 124.6, 121.9, 120.9, 118.1, 116.1, 102.4, 64.1, 45.1, 41.7,
28.3. M.F. C20H16ClN7O4; M. Wt. Cal: 453. Elemental analysis: Cal: C, 52.93; H, 3.55; N,
21.60; Found: C, 52.89; H, 3.50; N, 21.51.
6-Chloro-1-((1-((3-(8-methoxy-2H-chromen-3-yl)-1,2,4-oxadiazol-5-yl)methyl)-1H-1,2,3-
triazol-4-yl)methyl)-3-methylpyrimidine-2,4(1H,3H)-dione (5l): Off white solid; 78% yield;
M.P. 122–125 ◦C; 1H-NMR (400 MHz, CDCl3),
δ
, ppm: 7.96 (s, 1H), 7.44 (s, 1H), 6.90–6.75
(m, 3H), 5.97 (s, 1H), 5.84 (s, 2H), 5.39 (s, 2H), 5.22 (s, 2H), 3.90 (s, 3H), 3.32 (s, 3H). 13C-NMR
(100.6 MHz, CDCl3), , ppm: 171.4, 166.1, 160.6, 151.1, 147.9, 146.3, 145.2, 143.5, 143.0, 129.5,
δ
124.5, 121.6, 120.5, 118.2, 114.0, 102.4, 64.4, 56.1, 45.0, 41.7, 28.3. M.F. C21H18ClN7O5; M. Wt.
Cal: 483; Found: ESI-Ms m/z, 484 [M + H]+. Elemental analysis: Cal: C, 52.13; H, 3.75; N,
20.26; Found: C, 52.07; H, 3.69; N, 20.19.
6-Chloro-3-methyl-1-((1-(4-((4-methyl-2-oxo-2H-chromen-7-yl)oxy)butyl)-1H-1,2,3-triazol-4-
yl)methyl)pyrimidine-2,4(1H,3H)-dione (5m): Off white solid; 80% yield; M.P. 145–148 ◦C;