JOURNAL OF CHEMICAL RESEARCH 2013 339
+
7
.28–7.72 (m, 4H, ArH); ESI-MS m/z: 639 (M + H) . Anal. Calcd for
2,6-Bis[2-methylthio-5-morpholino7-oxothiazolo[4,5-d]pyrimidin-
6(7H)-yl]toluene (4k): White crystals; m.p. 267–269 °C; IR (KBr):
C H N O S : C, 52.64; H, 4.73; N, 17.54. Found: C, 52.57; H, 4.75;
28
30
8
2 4
−
1
1
N, 17.65%.
,4-Bis[5-(diethylamino)-2-methylthio-7-oxothiazolo[4,5-d]pyri-
midin-6(7H)-yl]toluene (4e): White crystals; m.p. > 300 °C; IR (KBr):
3296, 1687 (C=O), 1540, 1451, 1112, 1047 cm ; H NMR (CDCl ,
3
2
3
00 MHz): δ 2.35 (s, 3H, CH ), 2.47 (s, 6H, 2 × SCH ), 3.08 (t, J = 4.8
3
3
Hz, 8H, 4 × NCH ), 3.46 (t, J = 4.8 Hz, 8H, 4 × OCH ), 7.21–7.61 (m,
2
2
−
1
1
3
(
308, 2940, 1685 (C=O), 1552, 1458, 1343, 1212 cm ; H NMR
+
3
H, ArH); ESI-MS m/z: 657 (M + H) . Anal. Calcd for C H N O S :
27 28 8 4 4
CDCl , 300 MHz): δ 1.03 (t, J = 7.2 Hz, 12H, 4 × CH ), 2.34 (s, 3H,
3
3
C, 49.37; H, 4.30; N, 17.06. Found: C, 49.40; H, 4.21; N, 17.13%.
,6-Bis[2-methylthio-5- piperidino-7-oxothiazolo[4,5-d]pyrimidin-
(7H)-yl]toluene (4l): White crystals; m.p. > 300 °C; IR (KBr): 2978,
CH ), 2.47 (s, 6H, 2 × SCH ), 2.58 (q, J = 7.2 Hz, 8H, 4 × NCH ),
3
3
2
2
+
7
.23–7.51 (m, 3H, 3H, ArH); ESI-MS m/z: 629 (M + H) . Anal. Calcd
6
for C H N O S : C, 51.57; H, 5.13; N, 17.82. Found: C, 51.66; H,
27
32
8
2
4
−1
1
1
689 (C=O), 1553, 1457, 1248 cm ; H NMR (CDCl , 300 MHz):
3
5
.07; N, 17.71%.
,4-Bis[5-(diisopropylamino)-2-methylthio-7-oxothiazolo[4,5-d]pyri-
midin-6(7H)-yl]toluene (4f): White crystals; m.p. 265–266 °C;
δ 1.22–1.45 (m, 20H, 10 × CH ), 2.35 (s, 3H, CH ), 2.47 (s, 6H, 2 ×
2
3
2
+
SCH ), 7.28–7.72 (m, 4H, ArH); ESI-MS m/z: 653 (M + H) . Anal.
3
−
1
1
Calcd for C H N O S : C, 53.35; H, 4.94; N, 17.16. Found: C, 53.44;
IR (KBr): 3307, 2941, 1687 (C=O), 1553, 1415, 1221 cm ; H NMR
CDCl , 300 MHz): δ 1.05 (d, J = 7.2 Hz, 24H, 8 × CH ), 2.35 (s, 3H,
29 32
8
2 4
H, 4.86; N, 17.20%.
(
3
3
CH ), 2.47 (s, 6H, 2 × SCH ), 2.91–3.07 (m, 4H, 4CH), 7.24–7.64 (m,
3
3
+
3
H, ArH); ESI-MS m/z: 685 (M + H) . Anal. Calcd for C H N O S :
31 40 8 2 4
Received 10 February 2013; accepted 13 March 2013
Paper 1301789 doi: 10.3184/174751913X13668217942382
Published online: 12 June 2013
C, 54.36; H, 5.89; N, 16.36. Found: C, 54.27; H, 5.81; N, 16.33%.
,4-Bis[2-methylthio-5-morpholino-7-oxothiazolo[4,5-d]pyri-
midin-6(7H)-yl]toluene (4g): White crystals; m.p. 287–289 °C; IR
KBr): 3296, 1687 (C=O), 1540, 1451, 1112, 1047 cm ; H NMR
2
−1
1
(
(
(
-
CDCl , 300 MHz): δ 2.35 (s, 3H, CH ), 2.47 (s, 6H, 2 × SCH ), 3.08
References
3
3
3
t, J = 4.8 Hz, 8H, 4 × NCH ), 3.46 (t, J = 4.8 Hz, 8H, 4 × OCH ), 7.21
1
R.M. Shaker, Arkivoc, 2012 (i), 1.
2
2
+
7.61 (m, 3H, ArH); ESI-MS m/z: 657 (M + H) . Anal. Calcd for
2
A. Fernandez-Mato, G. Blanco, J.M. Quintela and C. Peinador, Tetrahedron,
C H N O S : C, 49.37; H, 4.30; N, 17.06. Found: C, 49.45; H, 4.19;
2008, 64, 3446.
27
28
8
4 4
N, 17.01%.
,4-Bis[2-methylthio-5- piperidino-7-oxothiazolo[4,5-d]pyrimidin-
(7H)-yl]toluene (4h): White crystals; m.p. > 300 °C; IR (KBr): 2978,
3
4
Y. Liang, H.W. He and Z.W. Yang, J. Heterocycl. Chem., 2011, 48, 88.
R.J. Zeng, Z.C. Zhou, Z.X. Wang and X.F. Li, Chin. J. Org. Chem., 2008,
28, 1624.
2
6
−
1
1
5
6
7
M. Chhabria, I. Rathod, K. Vala and P. Patel, Med. Chem. Res., 2011, 20,
1
689 (C=O), 1553, 1457, 1248 cm ; H NMR (CDCl , 300 MHz):
3
1
450.
Y. Liang, S. Fan, W.Y. Mo and H.W. He, J. Fluorine Chem., 2007, 128,
79.
δ 1.22–1.45 (m, 20H, 10 × CH ), 2.35 (s, 3H, CH ), 2.47 (s, 6H, 2 ×
2
3
+
SCH ), 7.28–7.72 (m, 4H, ArH); ESI-MS m/z: 653 (M + H) . Anal.
3
8
Calcd for C H N O S : C, 53.35; H, 4.94; N, 17.16. Found: C, 53.41;
29
32
8
2 4
N.S. Habib, R. Soliman, A. EI-Tombary, S. EI-Hawash and O.G. Shaaban,
Arch. Pharm. Res., 2007, 30, 1511.
A.M. Khairy and W.M. Basyouni, J. Sulfur Chem., 2010, 31, 551.
Q.Y. Ren, Y.J. Liang, H.W. He, L.W. Fu and Y.C. Gu, Bioorg. Med. Chem.
Lett., 2009, 19, 6713.
S. Peyman, I.M. David and D. Minoo, Mol. Divers., 2012, 16, 231.
G. Blanco and C. Peinador, Tetrahedron, 2008, 64, 1136.
C. Blackburn, A. Achab, A. Elder, S. Ghosh, J. Guo, G. Harriman and
M. Jones, J. Org. Chem., 2005, 70, 10206.
F. Palacios, C. Alonso, D.T. Aparicio, G. Rubiales and J. Santos,
Tetrahedron, 2007, 63, 523.
S. Pedeboscq, D. Gravier, F. Casadebaig, G. Hou, A. Gissot, F.D. Giorgi,
F. Ichas, J. Cambar and J.P. Pometan, Eur. J. Med. Chem., 2010, 45, 2473.
H, 4.87; N, 17.23%.
,6-Bis[5-(diethylamino)-2-methylthio-7-oxothiazolo[4,5-d]pyri-
midin-6(7H)-yl]toluene (4i): White crystals; m.p. > 300 °C; IR (KBr):
2
8
9
−
1
1
3
308, 2940, 1685 (C=O), 1552, 1458, 1343, 1212 cm ; H NMR
(
CDCl , 300 MHz): δ 1.03 (t, J = 7.2 Hz, 12H, 4 × CH ), 2.34 (s, 3H,
3
3
1
1
1
0
1
2
CH ), 2.47 (s, 6H, 2 × SCH ), 2.58 (q, J = 7.2 Hz, 8H, 4 × NCH ),
7
3
3
2
+
.23–7.51 (m, 3H, 3H, ArH); ESI-MS m/z: 629 (M + H) . Anal. Calcd
for C H N O S : C, 51.57; H, 5.13; N, 17.82. Found: C, 51.69; H,
27
32
8
2 4
5
.09; N, 17.77%.
,6-Bis[5-(diisopropylamino)-2-methylthio-7-oxothiazolo[4,5-d]pyri-
1
1
3
4
2
midin-6(7H)-yl]toluene (4j): White crystals; m.p. 265–266 °C; IR
−1
1
(
KBr): 3307, 2941, 1687 (C=O), 1553, 1415, 1221 cm ; H NMR
(
CDCl , 300 MHz): δ 1.05 (d, J = 7.2 Hz, 24H, 8 × CH ), 2.35 (s, 3H,
15 Z.D. Fang and J.Q. Liu, Chin. J. Org. Chem., 2011, 31, 2102.
16 Z.D. Fang and X.H. Wei, J. Chem. Res., 2012, 36, 612.
17 H. Wamhoff, S. Herrmann, S. Stolben and M. Nieger, Tetrahedron, 1993,
49, 581.
3
3
CH ), 2.47 (s, 6H, 2 × SCH ), 2.91–3.07 (m, 4H, 4CH), 7.24–7.64 (m,
3
3
3
+
H, ArH); ESI-MS m/z: 685 (M + H) . Anal. Calcd for C H N O S :
31 40 8 2 4
C, 54.36; H, 5.89; N, 16.36. Found: C, 54.29; H, 5.83; N, 16.31%.