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Hořejší, Pohl, Holý:
3-Methyl-9-pyrrolidin-1-yl-3H-imidazo[1,2-a]purine (5d ). Prepared from 3d . Ch rom atog-
raph ed in MeOH/CHCl3 6:94, yield 35 m g (7%) of brown crystals, m .p. 120–125 °C. MS (EI),
m/z (rel. in ten sity): 242 (100, M), 214 (48), 199 (13), 187 (30), 173 (53). HRMS (EI): for
C
12H14N6 calculated 242.1279, foun d 242.1265. UV (MeOH): 293 (2060), 285 (2340), 246
(22400). FT IR (KBr): 3417, 3093, 3029, 2955, 2924, 2853, 1620, 1585, 1542, 1518, 1457,
1396, 1351, 1244, 1143, 1048, 1031, 854, 758, 676, 603. 1H NMR (400 MHz, DMSO-d6): 1.98
(m , 4 H, pyrrolidin e CH2); 3.64 (s, 3 H, CH3-3); 4.20 (m , 4 H, pyrrolidin e CH2N); 7.36 (d,
1 H, J = 1.9, H-6); 7.95 (d, 1 H, J = 1.9, H-7); 8.02 (s, 1 H, H-2). 13C NMR (100.6 MHz,
DMSO-d6): 25.60 (pyrrolidin e CH2); 29.23 (CH3-3); 52.26 (pyrrolidin e CH2N); 108.32 (CH-7);
112.84 (C-9a); 131.62 (CH-6); 142.19 (C-9); 142.66 (CH-2); 150.57 (C-4a); 151.09 (C-3a).
For C12H14N6 (242.3) calculated: 59.49% C, 5.82% H, 34.69% N; foun d: 59.23% C, 6.06% H,
34.30% N.
N,N,1-Trimethyl-1H-imidazo[2,1-b]purin-4-amine (6a). Prepared from 3a. Ch rom atograph ed
in MeOH/CHCl3 2:98, yield 83 m g (19%) of yellow syrupy product. MS (EI), m/z (rel. in ten -
sity): 216 (100, M), 201 (39, M – CH3), 187 (56, M – NCH3), 172 (28, M – N(CH3)2. HRMS
(EI): for C10H12N6 calculated 216.1123, foun d 216.1111. UV (MeOH): 287 (7720), 238
(15040). FT IR (KBr): 3454, 3109, 3080, 2929, 1651, 1592, 1567, 1456, 1401, 1271, 1229,
1170, 1023, 876, 757, 649. 1H NMR (400 MHz, DMSO-d6): 3.42 (bs, 6 H, CH3); 4.07 (s, 3 H,
CH3-1); 7.27 (d, 1 H, J = 1.7, H-7); 7.85 (d, 1 H, J = 1.7, H-8); 7.92 (s, 1 H, H-2). 13C NMR
(100.6 MHz, DMSO-d6): 32.71 (CH3-1); 38.61 (CH3); 105.98 (CH-8); 116.30 (C-3a); 129.92
(CH-7); 134.72 (C-9a); 137.29 (CH-2); 148.08 (C-5a); 150.79 (C-4).
N,N-Diethyl-1-methyl-1H-imidazo[2,1-b]purin-4-amine (6b). Prepared from 3b. Ch rom atog-
raph ed in MeOH/CHCl3 5:95, yield 275 m g (56%) of sligh tly colored crystals, m .p. 110–115 °C.
MS (EI), m/z (rel. in ten sity): 244 (44, M), 229 (9, M – CH3), 215 (10, M – Et), 201 (29, M –
NEt), 188 (10), 172 (43, M – NEt2). HRMS (EI): for C12H16N6 calculated 244.1436, foun d
244.1437. UV (MeOH): 295 (6800), 238 (13020). FT IR (KBr): 3430, 3073, 2974, 2933, 1653,
1576, 1508, 1459, 1435, 1379, 1362, 1313, 1254, 1097, 1080, 1035, 900, 864, 760, 655.
1H NMR (400 MHz, DMSO-d6): 1.23 (t, 6 H, Jvic = 7.0, CH3); 3.99 (br, 4 H, CH2); 4.13 (s, 3 H,
CH3-1); 7.59 (d, 1 H, J = 2.3, H-7); 8.09 (d, 1 H, J = 2.3, H-8); 8.19 (s, 1 H, H-2). 13C NMR
(100.6 MHz, DMSO-d6): 13.60 (CH3); 33.06 (CH3-1); 43.37 (CH2); 108.04 (CH-8); 116.57
(C-3a); 122.20 (CH-7); 134.73 (C-9a); 139.13 (CH-2); 144.79 (C-5a); 150.68 (C-4). For
C
12H16N6 (244.3) calculated: 59.00% C, 6.60% H, 34.40% N; foun d: 58.72% C, 6.38% H,
34.63% N.
1-Methyl-9-pyrrolidin-1-yl-1H-imidazo[2,1-b]purine (6d ). Prepared from 3d . Ch rom atog-
raph ed in MeOH/CHCl3 6:94, yield 72 m g (15%) of sligh tly colored crystals, m .p. 215–218 °C.
MS (EI), m/z (rel. in ten sity): 242 (52, M), 213 (53), 178 (100). HRMS (EI): for C12H14N6 calcu-
lated 242.1279, foun d 242.1292. UV (MeOH): 288 (7400), 239 (15440). FT IR (KBr): 3409,
3103, 2955, 2921, 2875, 2853, 1648, 1581, 1507, 1451, 1348, 1267, 1228, 1058, 1025, 847,
759, 650. 1H NMR (400 MHz, DMSO-d6): 1.94 (bm , 4 H, pyrrolidin e CH2); 3.50–4.00 (bm ,
4 H, pyrrolidin e CH2N); 4.08 (s, 3 H, CH3-1); 7.31 (d, 1 H, J = 1.7, H-7); 7.88 (d, 1 H, J = 1.7,
H-8); 7.97 (s, 1 H, H-2). 13C NMR (100.6 MHz, DMSO-d6): 24.15 an d 25.30 (pyrrolidin e
CH2); 32.73 (CH3-1); 47.93 (pyrrolidin e CH2N); 106.26 (CH-8); 116.55 (C-3a); 128.41 (CH-7);
134.43 (C-9a); 138.04 (CH-2); 147.88 (C-5a); 149.32 (C-4). For C12H14N6 (242.3) calculated:
59.49% C, 5.82% H, 34.69% N; foun d: 59.17% C, 5.54% H, 34.82% N.
Collect. Czech. Chem. Commun. 2006, Vol. 71, No. 1, pp. 77–90