9, 7763. 6-chloro-8-(phenylethynyl)-9-(pyridin-2-ylmethyl)-9H-purine (28e) Light brown solid (19 mg76 (s, 2H) 13 C NMR (75 MHz, CDCl 3 ) ? 154 (ES+) m/z (%): 368.2 (100) [M+Na] + . 8-(phenylethynyl)-6-(phenylthio)-9-(tetrahydro-2H-pyran-2-yl)-9H-purine (28f) Beige solid (49.3 mg, 24%) : 1 H NMR (300 MHz, CDCl 3 ) ? 8.78 (s, 1H), 8.57 (d, J = 4.6 Hz, 1H), 7.67 (t, J = 8.5 Hz, 1H), 7.55 (d, J = 6.8 Hz, 2H), 7.49-7.37 (m, 3H) 37%): 1 H NMR (300 MHz, CDCl 3 ) ? 1 H NMR (300 MHz, CDCl 3 ) ? 8), 3.77 (t, J = 11.8 Hz, 1H), 3.01 (qd, J = 12.3, 4.0 Hz, 1H), 2.14 (d, J = 11.0 Hz, 1H), 1.95-1.64 (m, 4H). 13 C NMR (75 MHz) [M-THP] + . HRMS (ESI) calcd for C 24 H 21 N 4 OS [(M+H) + ] 413.1436, found 413.1437. 9-benzyl-6-(benzylthio)-8-(phenylethynyl)-9H-purine, pp.127527-127534, 1428. ,
13 C NMR (CDCl 3 , 75 MHz) ? 160.1, 156, HRMS (ESI) calcd for C 22 H 21 FN 5 OS [(M+H) + ] 422.1451, pp.85-88 ,
97 (s, 1H), 8.81 (d, J = 9, p.3184 ,
02 (m, 3H), 1.89-1.65 (m, 3H) 13 C NMR (75 MHz, CDCl 3 ) ? 162, HRMS (ESI)M+H) + ] 311.1508, pp.9085-9088 ,
90-1.67 (m, 3H) 13 C NMR (75 MHz, CDCl 3 ) ? 153, 9. MS (ES+) m/z (%): 349.1 (100) [M+H] + . HRMS (ESI)M+H) + ] 349.1276, pp.3-87 ,
(ESI) calcd for C 13 H 17 N 4 O [(M+H) + ] 245.1402, found 245.1398. 8-chloro-6-(4-methoxyphenyl)-9-(tetrahydro-2H-pyran-2-yl)-9H-purine (47b) Reaction conditions : 80 °C, 15 min Brown solid (24.3 mg, 30%) : mp = 128-130 °C. 1 H NMR (300 MHz, J = 8.9 Hz, 2H), 5.81 (dd, J = 11.3, 2.2 Hz, 1H), 4.23 (d), 3.03 (qd, J = 12.5, 4.0 Hz, 1H), 2.15 (m, 1H), 1.93-1.66 (m, 4H). 13 C NMR (75 MHz MS (ES+) m/z (%): 345.3 (100) [M+H] + , 261, pp.245-246, 1994. ,
89 (s, 1H)10 (d, J = 16, Hz, vol.8, issue.757, pp.68-75 ,
17-2.14 (m, 1H), 1.98-1.65 (m, 4H) 13 C NMR (75 MHz, CDCl 3 ) ? 162, 3H), 3.80 (t, J = 11.7 Hz, 1H), 3.07 (qd, J = 12.6, 4.4 Hz, 1H) HRMS (ESI) calcdM+H) + ] 411.1821, pp.4-2890 ,
13 C NMR (75 MHz, CDCl 3 ) ? 161, pp.8-10 ,
93 (s, 1H), pp.97-104 ,
13 C NMR (75 MHz, CDCl 3 ) ? 154 MS (ES+) m/z (%): 400.4 (100) [M+H] + . HRMS (ESI) calcd for C 24 H 26 N 5 O [(M+H) + ] 400.2137, found 400.2140. 8-phenyl-9-(tetrahydro-2H-pyran-2-yl)-6-(4-(trifluoromethyl)phenyl)-9H-purine (50c) Reaction conditions : 80 °C, 30 min, dd, J = 11.3, 2.1 Hz, 1H), 4.27 (d, J = 9.6 Hz, 1H), 9.00 (d, J = 8.4 Hz, 2H), 7.96-7.93 (m, 2H), 7.80 (d, J = 8.1 Hz, 2H) Hz, 1H), 3.22-3.11 (m, 1H), 2.08 (s, 1H), 1.89-1.63 (m, 4H). 13 C NMR (75 MHzM+H] + , 341.2 (70) [M-THP] + . HRMS (ESI) calcd for C 23 H 20 F 3 N 4 O [(M+H) + ] 425.1589, pp.70-73 ,
pour la référence et l'échantillon, l'absorbance et le spectre de fluorescence à la longueur d'onde d'excitation choisie de 4 solutions de concentration croissante ,
A) où F est l'intensité de fluorescence intégrée. La courbe obtenue doit être une droite passant par l'origine. ? F est alors calculé par la formule ,
65, 229. ? X ? QS Grad X ?² X Grad QS ?² QS (271 mg, 75%): 1 H NMR (300 MHz, CDCl 3 ) ? 7.58 (t, J = 7.7 Hz, 4H), 7.47?7.36 (m, 5H), p.81, 1961. ,
50 (d, J = 6.9 Hz, 2H), 7.34?7, pp.7-09 ,
55 (s, 2H), 4.70 (s, 2H), 3.91 (s, 3H), 3.90 (s, 3H); 13 C NMR (75 MHz, CDCl 3 ) ? 158, pp.96-495 ,
13 C NMR (75 MHz, CDCl 3 ) ? 159 (E)-9-Benzyl-6-(benzylthio)-8-(3-bromostyryl)-9H-purine (3g) A yellow solid (107 mg, 57%): mp = 182?184 °C (ES+) m/z (%) 513 (ESI) calcd for C 27 H 22, 63?7.55 (ESI) C 28 H 22 F 3 N 4 S calcd for [(M + H) + ] 503.1517, found 503.1497 (E)-4-(2-(9-Benzyl-6-(benzylthio)-9H-purin-8-yl)vinyl)- benzonitrile (3h). A yellow solid (105 mg, 63%): mp = 206?208 °C; 1 H NMR (300 MHz, CDCl 3 ) ? 8.75 (s, 1H)), 7.03 (d, J = 15.8 Hz, 1H), 5.57 (s, 2H), 4.70 (s, 2H); 13 C NMR (75 MHz, pp.7-35, 1994. ,
CDCl 3 ) ? 159 (ES+) m/z (%) 480.2 (100))styryl)-9H- purine (3j). A yellow oil (86 mg, 44%): 1 H NMR (300 MHz, C NMR (75 MHz CDCl 3 ) ? 8.72 (s, 1H), 8.03 (d, J = 15.8 Hz, 1H) Hz, 1H), 5.55 (s, 2H), 5.50 (s, 1H), 4.70 (s, 2H), 3.64?3.51 (m, 4H), 1.28?1.18 (m, 6H), p.597075 ,
HRMS (ESI) calcd for C 32 H 33 N 42324, found 537.2305. 9-Benzyl-6-(benzylthio)-8-(1-phenylvinyl)-9H-purine (3k). ?- Bromostyrene was distilled before use. A yellow solid (79 mg, 50%): mp = 128?130 °C75 (s, 1H), 5.08 (s, 2H), 4.70 (s, 2H); 13 C NMR (75 MHz, CDCl 3 ) ? 159 A yellow oil obtained as an inseparable mixture A brown solid, H NMR (300 MHz, CDCl 3 ) ? 8.78 (s, 1H), 7.50 (d, J = 7.0 Hz, 2H), 7.33?7.18 (m, 11H), 6.95?6.92 (m, 2H), 5.93 (s, 1H)70) [M + Na] + . HRMS (ESI) calcd for C 27 H 23 N 4 S [(M + H) + ] 435.1643, found 435.1627. (Z)-9-Benzyl-6-(benzylthio)-8-(4-methylstyryl)-9H-purine (3l)m, 9H), 7.08?7.05 (m, 4H), 6.93 (d, J = 12.6 Hz, 1H), 6.35 (d, J = 12.6 Hz, 1H), 5.16 (s, 2H), 4.69 (s, 2H), 2.30 (s, 3H); 13 C NMR (75 MHz MS (ES+) m/z (%): 449.5 (100) [M + H] + . HRMS (ESI) and 10 49 showed satisfactory spectroscopic data in agreement with those reported in the literature. (E)-2-Phenyl-5-styryl-1, p.334 ,
MS (ES +) m/z (%) 271.1 (100) [M + Na] + . HRMS (ESI) calcd for C General Procedure for the Amination As Illustrated for the Preparation of (E)-N,9-Dibenzyl-8-styryl-9H-purin-6-amine (12a). A solution of m-CPBA, C NMR (75 MHz, p.1 ,
(E)-9-Benzyl-N-propyl-8-styryl-9H-purin-6-amine (12b) Propylamine was distilled before use Reaction time: 1 h. A yellow oil (125.2 mg, 79%): 1 H NMR (300 MHz, CDCl 3 ) ? 8.40 (s, 1H), 7.77 (d, J = 15.9 Hz, 1H), 7.46 (d, J = 7.6 Hz, 2H), 7.37?7.23 (m, 8H), 6.96 (d, J = 15.9 Hz, 1H), 5.99 (bs, 1H), p.5066 ,
CDCl 3 ) ? 8.37 (s, 1H), p.47 ,
96 (d, J = 1506 (bs, 4H); 13 C NMR (75 MHz, CDCl 3 ) ? 152, 5.51 (s, 2H), 4.29 (bs, 2H), 3.81 (bs, 2H)) [M + H] + . HRMS (ESI) calcd, pp.7-38 ,
CDCl 3 ) ? 8.41 (s, 1H), p.47 ,
(ES+) m/z (%): 427, HRMS (ESI) ,
Supporting Information Copies of 1 H and 13 C for all compounds 1, 2c, 2j, 3a?l, 4?10, and 12a?g. This material is available free of charge via the Internet at http://pubs ,
thank the Ministe? re de l?Enseignement Supe?rieurSupe?rieur et de la Recherche for doctoral fellowships ,
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