Molecules 2005, 10
52.8 (C2’), 153.7 and 149.0 (C4’ and C6’), 140.7 (C8’), 118.5 (C5’), 72.1 (NCH
513
1
2
O), 70.7
-
1
(
2 2 2 2
HOCH CH O), 59.8 (HOCH CH O), 48.6 (NCH), 32.3, 25.1, 24.9 (CyH); IR (ATR, cm ): 3323 (m),
2
927 (m), 1615 (s), 1478 (m), 1343 (m), 1293 (m), 1217 (m), 1114 (m), 754 (m); MS (EI, 70 eV): m/z
+
(
%) = 291 (8) [M ], 216 (19), 209 (50), 174 (24), 160 (26), 148 (26), 135 (100)55 (17); HRMS (EI, 70
+
EV) calcd. for [M ] C14
H
21
N
5
O
2
: 291.1695, found: 291.169.
2
-(6’-Phenylamino-purin-9’-ylmethoxy)-ethanol (13): The acyclic nucleoside analog 13 was prepared
according to the general protocols for the amination of 5 using conditions A, B or C (for yields see
1
Table 1). M.p. 169 °C; TLC: R
f
= 0.27 (EtOAc/MeOH 10:1); H-NMR (250 MHz): δ = 9.90 (s, 1H,
NH), 8.46 and 8.44 (2s, 2H, H-2’ and H-8’), 7.95 (d, J = 7.8 Hz, 2H, Har), 7.33 (t, J = 7.7 Hz, 2H, Har),
7
.04 (t, J = 7.3 Hz, 1H, Har), 5.64 (s, 2H, NCH
2
O), 4.69 (t, J = 5.3 Hz, 1H, OH), 3.58-3.46 (m, 4H,
O); C-NMR (63 MHz): δ = 152.3 (C2’), 152.0 and 149.8 (C4’ and C6’), 142.0 (C8’),
O), 70.8 (HOCH CH O), 59.8
1
3
2 2
HOCH CH
139.5 (s, Car), 128.3, 122.5, 120.7 (d, Car), 119.5 (C5’), 72.3 (NCH
2
2
2
-
1
(
(
(
HOCH
2
CH
2
O); IR (ATR, cm ): 3322 (m), 1621 (s), 1580 (s), 1496 (m), 1477 (m), 1115 (m), 753
+
m); MS (EI, 70 eV): m/z (%) = 285 (21) [M ], 240 (8), 224 (30), 211 (41), 210 (100), 77 (23); HRMS
+
EI, 70 eV) calcd. for [M ] C14
H
15
N
5
O
2
: 285.1226, found: 285.122.
2
-(6’-Benzylamino-purin-9’-ylmethoxy)-ethanol (14) [10]: The acyclic nucleoside analog 14 was
prepared according to the general protocols for the amination of 5 using conditions A, B or C (for
yields see Table 1). M.p. 111 °C (lit. [10]: 113-114 °C); TLC: R
f
= 0.22 (EtOAc/MeOH 10:1);
1
H- NMR (250 MHz): δ = 8.38 (s, 1H, NH), 8.30 and 8.24 (2s, 2H, H-2’ and H-8’), 7.36-7.18 (m, 5H,
H
ar), 5.58 (s, 2H, NCH
2
O), 4.72 (s, 2H, NCH
O); C-NMR (63 MHz): δ = 154.3 and 152.7 (C4’ and C6’), 154.3 (C2’), 141.0 (C8’),
O), 70.7 (HOCH CH O), 59.8
2
Car), 4.67 (t, J = 5.2 Hz, 1H, OH), 3.54-3.46 (m, 4H,
1
3
2 2
HOCH CH
139.9 (s, Car), 128.1, 127.0, 126.5 (d, Car), 118.8 (C5’), 72.2 (NCH
2
2
2
-
1
(
HOCH
2
CH
2
O), 42.8 (NCH
2
C
ar); IR (ATR, cm ): 3283 (m), 2926 (m), 1616 (s), 1482 (m), 1343 (m),
+
1
2
217 (m), 1114 (m), 1073 (m), 761 (m), 645 (m); MS (EI, 70 eV): m/z (%) = 299 (39) [M ], 254 (8),
38 (16), 225 (66), 224 (91), 120 (26), 106 (95), 91 (100), 79 (16), 65 (25); HRMS (EI, 70 eV) calcd.
+
for [M ] C15
H
17
N
5
O
2
: 299.1382, found: 299.138.
2
-[6’-(p-Morpholinyl-phenylamino)-purin-9’-ylmethoxy]-ethanol (15): The acyclic nucleoside analog
1
5 was prepared according to the general protocols for the amination of 5 using conditions A, B or C
1
(
for yields see Table 1). M.p. 186 °C; TLC: R
f
= 0.16 (EtOAc/MeOH 10:1); H-NMR (250 MHz): δ =
9
.69 (s, 1H, NH), 8.41 and 8.36 (2s, 2H, H-2’ and H-8’), 7.74 (d, J = 9.0 Hz, 2H, Har), 6.92 (d, J = 9.0
O), 4.68 (t, J = 5.3 Hz, 1H, OH), 3.74 (t, J = 4.8 Hz, 4H, NCH CH O),
O); C-NMR (63 MHz): δ =
52.4 (C2’), 152.1 and 149.5 (C4’ and C6’), 147.0 (s, Car), 141.6 (C8’), 131.6 (s, Car), 122.2 (d, Car),
19.2 (C5’), 115.2 (d, Car), 72.3 (NCH O), 70.8 (HOCH CH O), 66.0 (NCH CH O), 59.8
Hz, 2H, Har), 5.62 (s, 2H, NCH
2
2
2
1
3
3
1
1
2 2 2 2
.56-3.45 (m, 4H, HOCH CH O), 3.06 (t, J = 4.8 Hz, 4H, NCH CH
2
2
2
2
2
-
1
(
(
(
HOCH
2
CH
2
O), 49.0 (NCH
2
CH
2
O); IR (ATR, cm ): 3323 (m), 2922 (m), 1618 (s), 1583 (m), 1511
+
s), 1477 (m), 1230 (m), 1117 (m), 926 (m), 758 (m); MS (EI, 70 eV): m/z (%) = 270 (100) [M ], 309
+
10), 296 (67), 238 (57), 209 (12), 155 (7), 125 (19), 77 (10); HRMS (EI, 70 eV) calcd. for [M ]
18 22 6 3
C H N O : 370.1753, found: 370.175.