Table3.: Yields, melting points, data of TLC and
elemental analysis of 4-methyl-2-mercapto-6-perfluoro-substituted pyrimidines (19-24).
N |
Yields, % |
M.p. ° C |
Rfa |
Found, %
|
Formula |
Calculated,
% |
F
|
S
|
F |
S |
19 |
60 |
114-116 |
0.59 |
55.62 |
7.20 |
C11H5F13N2S |
55.60 |
7.22 |
20 |
51 |
Amorphous |
0.67 |
59.35 |
5.88 |
C13H5F17N2S |
59.34 |
5.89 |
21 |
39 |
94-96 |
0.65 |
50.98 |
7.84 |
C10H5F11N2SO |
50.94 |
7.82 |
22 |
45 |
Amorphous |
0.92 |
56.12 |
5.59 |
C13H5F17N2SO2 |
56.05 |
5.57 |
23 |
57 |
Oil |
0.79 |
58.92 |
4.34 |
Cl6H5F23N2SO3 |
58.87 |
4.32 |
24 |
70 |
oil |
0.91 |
- |
- |
C37H5F65N2SO10
(n=9) |
- |
- |
a TLC: Silufol UV-254, eluent CHCl3-ethanol
1:1.
Table6.: Spectral characteristics of
4-methyl-2-mercapto-6-perfluoro-substituted pyrimidines (19-24)
| N |
IR - spectra |
UV-spectra
(i-propanol) |
PMR-spectra
(CD3OD), d |
| n CH, |
n SH |
n C=C, n C=O |
n C=N d NH |
n CF (n C=S) |
l max, nm |
lge |
|
| 19 |
3380 3250
3100
2900 |
2500 2350 |
1690 1600 |
1680 1540 |
1320- 1020 (790- 665) |
235 |
3.92 |
2.80 t
(3H, CH3), 7.05 d (1H, C5H), 8.45 (broad)(1H, NH) |
| 20 |
2980 2760 |
2310 |
1770 1450 |
1590 1430 |
1390- 970, (805, 635) |
212 |
- |
- |
| 21 |
3350 3200
3130 |
2400 |
1770 1640
1540 |
1660 1610 |
1380- 990, (769, 666) |
235 |
4.29 |
2.68t (3H, CH3), 7.15
d (1H, C5H), 8.88 (broad)(1H, NH) |
| 22 |
3340 3170
2993 |
2490 |
1777 1558 |
1668 1526 |
1333-1107, (744, 709) |
206 |
3.80 |
- |
| 23 |
330 3200 |
2500 |
1770 1540 |
1660 |
1330-995 (715, 610) |
202, 217 |
2.74, 3.01 |
2.25t
(3H, CH3), 7.10 (broad) (1H, C5H), 8.88 (broad)(1H, NH) |
| 24 |
3308 2992
2944
2528 |
2352 |
1776 1550 |
1718 1450 |
1390- 950 (810, 770) |
202, 217 |
3.14, 3.35 |
- |
|