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3H), 2.57 (s, 1H), 1.87–1.99 (m, 4H); 13C NMR (100 MHz, 127.2 (t, JC–F ¼ 10 Hz), 114.5 (t, JC–F ¼ 16 Hz), 113.1, 111.7 (dd,
CD3OD) d 173.7, 160.6 (dd, JC–F ¼ 248 Hz, 4 Hz, 2C), 157.2 JC–F ¼ 18 Hz, 5 Hz, 2C), 110.0, 109.6, 63.8, 55.9, 46.1 (2C); HR-
(d, JC–F ¼ 2 Hz), 153.1 (d, JC–F ¼ 12 Hz), 143.7 (d, JC–F ¼ 245 Hz), ESI-MS: m/z ¼ 447.1739 [M + H]+, calcd for C21H22F3N6O2:
142.3, 141.1 (d, JC–F ¼ 20 Hz), 139.6, 129.7, 129.1 (t, JC–F ¼ 10 447.1751.
Hz), 116.4 (t, JC–F ¼ 17 Hz), 116.3, 114.9, 112.8 (dd, JC–F ¼ 18 Hz,
N-(5-((4-((2,6-Diuorophenyl)amino)-5-uoropyrimidin-2-yl)-
(3i).
Yield: 36%, mp: 203–205 ꢁC, 1H NMR (400 MHz, CDCl3) d 9.48
5 Hz, 2C), 112.2, 54.9 (2C), 44.0, 41.5, 27.7 (2C); HR-ESI-MS: m/z amino)-2-methoxyphenyl)-2-(dimethylamino)acetamide
¼ 457.1950 [M + H]+, calcd for C23H24F3N6O: 457.1958.
3-((4-((2,6-Diuorophenyl)amino)-5-uoropyrimidin-2-yl)- (s, 1H), 8.21 (d, J ¼ 2.8 Hz, 1H), 7.97 (d, J ¼ 2.8 Hz, 1H), 7.44 (dd,
amino)-N-(2-(dimethylamino)ethyl)benzamide (3e). Yield: 47%, J ¼ 8.8 Hz, 2.4 Hz, 1H), 7.22–7.29 (m, 1H), 7.01 (t, J ¼ 7.6 Hz,
mp: 190–192 ꢁC, 1H NMR (400 MHz, CDCl3) d 8.01 (d, J ¼ 2.8 Hz, 2H), 6.74 (s, 1H), 6.71 (d, J ¼ 8.8 Hz, 1H), 6.24 (s, 1H), 3.84 (s,
1H), 7.53–7.81 (m, 2H), 7.34 (d, J ¼ 7.6 Hz, 1H), 7.28–7.30 (m, 3H), 3.11 (s, 2H), 2.40 (s, 6H); 13C NMR (125 MHz, CDCl3)
1H), 7.21 (t, J ¼ 7.6 Hz, 1H), 7.03 (t, J ¼ 8.0 Hz, 2H), 6.93 (s, 1H), d 167.6, 158.5 (dd, JC–F ¼ 250 Hz, 5 Hz, 2C), 155.6 (d, JC–F ¼ 3 Hz),
6.82 (s, 1H), 6.33 (s, 1H), 3.54 (t, J ¼ 5.6 Hz, 2H), 2.55 (t, J ¼ 150.8 (d JC–F ¼ 11 Hz), 141.9 (d, JC–F ¼ 246 Hz), 141.3 (d, JC–F
¼
5.6 Hz, 2H), 2.30 (s, 6H); 13C NMR (125 MHz, CDCl3) d 167.6, 19 Hz), 140.3, 135.6, 129.0, 127.7 (t, JC–F ¼ 10 Hz), 121.5, 120.5,
158.5 (dd, JC–F ¼ 250 Hz, 5 Hz, 2C), 155.6 (d, JC–F ¼ 3 Hz), 150.8 117.6, 114.5 (t, JC–F ¼ 15 Hz), 111.9 (dd, J ¼ 19 Hz, 4 Hz, 2C),
(d, JC–F ¼ 11 Hz), 141.9 (d, JC–F ¼ 246 Hz), 141.3 (d, JC–F ¼ 19 Hz), 58.0, 45.3 (2C), 37.4; HR-ESI MS: m/z ¼ 447.1734 [M + H]+, calcd
140.3, 135.6, 129.0, 127.7 (t, JC–F ¼ 10 Hz), 121.5, 120.5, 117.6, for C21H22F3N6O2: 447.1751.
114.5 (t, JC–F ¼ 15 Hz), 111.9 (dd, JC–F ¼ 19 Hz, 4 Hz, 2C), 58.0,
N-(5-((4-((2,6-Diuorophenyl)amino)-5-uoropyrimidin-2-yl)-
45.3 (2C), 37.4; HR-ESI-MS: m/z ¼ 431.1797 [M + H]+, calcd for amino)-2-methylphenyl)-2-(dimethylamino)acetamide
(3j).
C
21H22F3N6O: 431.1802.
Yield: 51%, mp: 215–216 ꢁC, 1H NMR (400 MHz, DMSO-d6)
N-(3-((4-((2,6-Diuorophenyl)amino)-5-uoropyrimidin-2-yl)- d 9.18 (s, 1H), 9.13 (s, 1H), 9.05 (s, 1H), 8.08 (d, J ¼ 3.6 Hz,
amino)-4-uorophenyl)-2-(dimethylamino)acetamide
(3f). 1H), 7.55 (s, 1H), 7.39–7.45 (m, 1H), 7.27 (dd, J ¼ 8.4 Hz, 2.4 Hz,
Yield: 55%, mp: 204–205 ꢁC, 1H NMR (400 MHz, DMSO- d6) 1H), 7.21 (t, J ¼ 8.0 Hz, 2H), 6.82 (d, J ¼ 8.4 Hz, 1H), 3.03 (s, 2H),
d 9.50 (s, 1H), 9.16 (s, 1H), 8.46 (s, 1H), 8.03 (d, J ¼ 3.2 Hz, 1H), 2.30 (s, 6H), 2.06 (s, 3H); 13C NMR (100 MHz, CDCl3) d 168.3,
7.68 (dd, J ¼ 7.2 Hz, 2.0 Hz, 1H), 7.30–7.38 (m, 2H), 7.14 (t, J ¼ 158.3 (dd, JC–F ¼ 249 Hz, 5 Hz, 2C), 155.6 (d, JC–F ¼ 3 Hz), 150.4
8.0 Hz, 2H), 7.00 (t, J ¼ 9.6 Hz, 1H), 3.04 (s, 2H), 2.27 (s, 6H); 13C (d, JC–F ¼ 11 Hz), 141.5 (d, JC–F ¼ 245 Hz), 141.1 (d, JC–F ¼ 19 Hz),
NMR (100 MHz, CDCl3) d 168.7, 158.4 (dd, JC–F ¼ 249 Hz, 4 Hz, 138.5, 135.7, 130.3, 127.3 (t, JC–F ¼ 10 Hz), 120.9, 114.7, 114.5 (t,
2C), 155.1 (d, JC–F ¼ 3 Hz), 150.8 (d, JC–F ¼ 12 Hz), 149.0 (d, JC–F
¼
JC–F ¼ 16 Hz), 111.7 (dd, JC–F ¼ 18 Hz, 5 Hz, 2C), 111.7, 63.7, 46.0
249 Hz), 142.0 (d, JC–F ¼ 247 Hz), 140.9 (d, JC–F ¼ 19 Hz), 133.8 (2C), 16.9; HR-ESI-MS: m/z ¼ 431.1786 [M + H]+, calcd for
(d, JC–F ¼ 2 Hz), 128.5 (d, JC–F ¼ 11 Hz), 127.5 (t, JC–F ¼ 10 Hz),
114.7 (d, JC–F ¼ 20 Hz), 114.3 (t, JC–F ¼ 16 Hz), 113.4 (d, JC–F ¼ 7
C
21H22F3N6O: 431.1802.
N-(4-((4-((2,6-Diuorophenyl)amino)-5-uoropyrimidin-2-yl)-
Hz), 111.8 (dd, JC–F ¼ 18 Hz, 5 Hz, 2C), 111.1, 63.8, 46.1 (2C); HR- amino)phenyl)-2-(dimethylamino)acetamide (3k). Yield: 74%,
ESI-MS: m/z ¼ 435.1542 [M + H]+, calcd for C20H19F4N6O: mp: 225–227 ꢁC, 1H NMR (400 MHz, CDCl3) d 8.97 (s, 1H), 7.97
435.1551.
(d, J ¼ 2.8 Hz, 1H), 7.38 (d, J ¼ 8.8 Hz, 2H), 7.33 (d, J ¼ 8.8 Hz,
N-(5-((4-((2,6-Diuorophenyl)amino)-5-uoropyrimidin-2-yl)- 2H), 7.27–7.29 (m, 1H), 7.03 (t, J ¼ 8.4 Hz, 2H), 6.88 (s, 1H), 6.31
amino)-2-uorophenyl)-2-(dimethylamino)acetamide
(3g). (s, 1H), 3.07 (s, 2H), 2.38 (s, 6H); 13C NMR (100 MHz, CDCl3)
1
ꢁ
Yield: 40%, mp: 169–171 C, H NMR (400 MHz, CDCl3) d 9.41 d 168.5, 158.5 (dd, JC–F ¼ 249 Hz, 4 Hz, 2C), 155.7 (d, JC–F ¼ 3 Hz),
(s, 1H), 8.14 (dd, J ¼ 6.8 Hz, 2.4 Hz, 1H), 7.99 (d, J ¼ 3.2 Hz, 1H), 150.6 (d, JC–F ¼ 12 Hz), 141.5 (d, JC–F ¼ 246 Hz), 141.3 (d, JC–F
¼
7.42–7.46 (m, 1H), 7.23–7.32 (m, 1H), 7.02 (t, J ¼ 8.0 Hz, 2H), 20 Hz), 136.2, 132.1, 127.6 (t, JC–F ¼ 10 Hz), 120.0 (2C), 119.1
6.85–6.90 (m, 2H), 6.27 (s, 1H), 3.15 (s, 2H), 2.42 (s, 6H); 13C (2C), 114.5 (t, JC–F ¼ 16 Hz), 111.9 (dd, JC–F ¼ 18 Hz, 5 Hz, 2C),
NMR (100 MHz, CDCl3) d 168.9, 158.3 (dd, JC–F ¼ 249 Hz, 5 Hz, 63.7, 46.1 (2C); HR-ESI-MS: m/z ¼ 417.1629 [M + H]+, calcd for
2C), 155.5 (d, JC–F ¼ 3 Hz), 150.5 (d, JC–F ¼ 12 Hz), 147.9 (d, JC–F
¼
C20H20F3N6O: 417.1645.
238 Hz), 141.6 (d, JC–F ¼ 246 Hz), 141.1 (d, JC–F ¼ 19 Hz), 136.1
N-(2-((4-((2,6-Diuorophenyl)amino)-5-uoropyrimidin-2-yl)-
(d, JC–F ¼ 3 Hz), 127.4 (t, JC–F ¼ 10 Hz), 125.9 (d, JC–F ¼ 11 Hz), amino)phenyl)-2-(dimethylamino)acetamide (3l). Yield: 28%,
114.5 (d, JC–F ¼ 19 Hz), 114.4 (t, JC–F ¼ 16 Hz), 114.3 (d, JC–F ¼ 7 mp: 192–193 ꢁC, 1H NMR (400 MHz, CDCl3) d 9.44 (s, 1H), 7.94
Hz), 111.8 (d, JC–F ¼ 6 Hz), 111.7 (dd, JC–F ¼ 18 Hz, 5 Hz, 2C), (d, J ¼ 2.4 Hz, 1H), 7.69 (d, J ¼ 7.6 Hz, 1H), 7.43 (d, J ¼ 7.6 Hz,
63.7, 46.0 (2C); HR-ESI-MS: m/z ¼ 435.1538 [M + H]+, calcd for 1H), 7.18–7.23 (m, 1H), 7.12 (t, J ¼ 7.6 Hz, 1H), 7.09 (t, J ¼ 7.6 Hz,
C
20H19F4N6O: 435.1551.
1H), 6.95 (t, J ¼ 8.0 Hz, 2H), 6.87 (s, 1H), 6.27 (s, 1H), 3.07 (s,
N-(3-((4-((2,6-diuorophenyl)amino)-5-uoropyrimidin-2-yl)- 2H), 2.27 (s, 6H); 13C NMR (100 MHz, CDCl3) d 169.2, 158.2 (dd,
amino)-4-methoxyphenyl)-2-(dimethylamino)acetamide (3h). JC–F ¼ 248 Hz, 4 Hz, 2C), 156.5 (d, JC–F ¼ 3 Hz), 150.7 (d, JC–F ¼ 11
1
ꢁ
Yield: 68%, mp: 200–202 C, H NMR (400 MHz, CDCl3) d 8.73 Hz), 141.7 (d, JC–F ¼ 245 Hz), 141.2 (d, JC–F ¼ 19 Hz), 131.3,
(s, 1H), 8.10 (s, 1H), 8.04 (s, 1H), 7.52 (d, J ¼ 8.8 Hz, 1H), 7.43 (s, 131.2, 127.4 (t, JC–F ¼ 10 Hz), 125.4, 125.3, 124.9, 123.7, 114.1 (t,
1H), 7.21–7.24 (m, 1H), 7.06 (t, J ¼ 8.4 Hz, 2H), 6.79 (d, J ¼ JC–F ¼ 16 Hz), 111.7 (dd, JC–F ¼ 18 Hz, 5 Hz, 2C), 63.2, 45.7 (2C);
8.8 Hz, 1H), 6.34 (s, 1H), 3.83 (s, 3H), 3.12 (s, 2H), 2.42 (s, 6H); HR-ESI-MS: m/z ¼ 417.1635 [M + H]+, calcd for C20H20F3N6O:
13C NMR (100 MHz, CDCl3) d 168.4, 158.2 (dd, JC–F ¼ 249 Hz, 417.1645.
4 Hz, 2C), 155.4 (d, JC–F ¼ 3 Hz), 150.5 (d, JC–F ¼ 11 Hz), 144.5,
141.6 (d, JC–F ¼ 246 Hz), 141.0 (d, JC–F ¼ 19 Hz), 130.8, 129.6,
11882 | RSC Adv., 2018, 8, 11871–11885
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