A. Kurimoto et al. / Bioorg. Med. Chem. 11 (2003) 5501–5508
5505
2-Amino-9-benzyl-8-hydroxyadenine (9a). A colorless
solid (11% for three steps from 6), mp 267–268 ꢀC; H
(M+); HRMS calcd for C16H20N6O 312.1698, found
312.1723. Anal. calcd for C16H20N6O 1/4H2O: C, 60.65;
H, 6.52; N, 26.52. Found: C, 60.70; H, 6.33; N, 26.53.
1
.
NMR (DMSO-d6) d 9.63 (1H, s), 7.34–7.22 (5H, m),
6.02 (2H, s), 5.74 (2H, s), 4.81 (2H, s); MS (EI) m/z 256
(M+); HRMS calcd for C12H12N6O 256.1072, found
256.1089. Anal. calcd for C12H12N6O: C, 56.24; H, 4.72;
N, 32.79. Found: C, 56.07; H, 4.62; N, 32.78.
9-Benzyl-2-(cyclohexylamino)-8-hydroxyadenine (9i). A
colorless solid (9% for three steps from 6), mp 245–
248 ꢀC; H NMR (DMSO-d6) d 9.62 (1H, s), 7.28 (5H,
1
m), 5.96 (3H, s), 4.78 (2H, s), 3.58 (1H, m), 1.80 (2H,
m), 1.65 (2H, m), 1.56 (1H, m), 1.27–1.06 (5H, m); MS
(EI) m/z 338 (M+); HRMS calcd for C18H22N6O
9-Benzyl-2-(ethylamino)-8-hydroxyadenine (9c). A color-
less solid (46% for three steps from 6), mp 269–272 ꢀC;
1H NMR (DMSO-d6) d 9.65 (1H, s), 7.34–7.24 (5H, m),
6.18 (1H, t, J=5.5 Hz), 6.01 (2H, s), 4.81 (2H, s), 3.19
(2H, m), 1.06 (3H, t, J=7.1 Hz); MS (EI) m/z 284
(M+); HRMS calcd for C14H16N6O 284.1385, found
338.1855,
found
338.1842.
Anal.
calcd
for
.
C18H22N6O 3/4H2O: C, 61.43; H, 6.73; N, 23.88.
Found: C, 61.72; H, 6.74; N, 23.95.
.
284.1363. Anal. calcd for C14H16N6O 1/4H2O: C, 58.22;
H, 5.76; N, 29.10. Found: C, 58.45; H, 5.64; N, 29.23.
9-Benzyl-8-hydroxy-2-[(2-methoxyethyl)amino]adenine
(9o). A colorless solid (19% for three steps from 6), mp
218–220 ꢀC; H NMR (DMSO-d6) d 9.66 (1H, s), 7.34–
1
9-Benzyl-2-(butyllamino)-8-hydroxyadenine (9d). A col-
orless solid (75% for three steps from 6), mp 248–250 ꢀC;
1H NMR (DMSO-d6) d 9.64 (1H, s), 7.29–7.24 (5H, m),
6.19 (1H, t, J=6.2 Hz), 6.00 (2H, s), 4.80 (2H, s), 3.15 (2H,
m), 1.43 (2H, m), 1.28 (2H, m), 0.87 (3H, t, J=7.3 Hz);
MS (EI) m/z 312 (M+); HRMS calcd for C16H20N6O
312.1698, found 312.1671. Anal. calcd for C16H20N6O 1/
2H2O: C, 59.80; H, 6.59; N, 26.15. Found: C, 59.71; H,
6.55; N, 25.88.
7.26 (5H. m), 6.14 (1H, t, J=7.8 Hz), 6.05 (2H, s), 3.37
(4H, m), 3.22 (3H, s); MS (EI) m/z 314 (M+); HRMS
calcd for C15H18N6O2 314.1491, found 314.1476. Anal.
calcd for C15H18N6O2 1/10H2O: C, 56.99; H, 5.80; N,
26.58. Found: C, 56.96; H, 5.70; N, 26.37.
.
.
9-Benzyl-2-(benzylamino)-8-hydroxyadenine (9q). A col-
orless solid (8% for three steps from 6), mp 241–242 ꢀC;
1H NMR (DMSO-d6) d 9.75 (1H, s), 7.31–7.15 (10H,
m), 6.83 (1H, t, J=6.4 Hz), 6.10 (2H, s), 4.78 (2H, s),
4.40 (2H, d, J=6.4 Hz); MS (FAB) m/z 347 (MH+);
HRMS calcd for C19H19N6O 347.1620, found 347.1625.
9-Benzyl-8-hydroxy-2-(pentylamino)adenine (9e). A col-
orless solid (37% for three steps from 6), mp 250–
252 ꢀC; H NMR (DMSO-d6) d 9.63 (1H, s), 7.30–7.24
1
(5H, m), 6.19 (1H, t, J=5.3 Hz), 5.99 (2H, s), 4.80 (2H,
s), 3.19–3.11 (2H, m), 1.48–1.43 (2H, m), 1.27-1.24 (4H,
m), 0.85 (3H, t, J=7.0 Hz); MS (EI) m/z 326 (M+);
HRMS calcd for C17H22N6O 326.1855, found 326.1872.
Anal. calcd for C17H22N6O 1/4H2O: C, 61.71; H, 6.85;
N, 25.40. Found: C, 61.54; H, 6.73; N, 25.39.
2-Anilino-9-benzyl-8-hydroxyadenine (9r). A colorless
solid (13% for three steps from 6), mp 220–223 ꢀC; H
1
NMR (DMSO-d6) d 9.88 (1H, s), 8.79 (1H, s), 7.67 (2H,
d, J=8.0 Hz), 7.30–7.17 (5H, m), 7.11 (2H, t, J=8.0
Hz), 6.75 (1H, t, J=8.0 Hz), 6.20 (2H, s), 4.83 (2H, s);
MS (FAB) m/z 333 (MH+); HRMS calcd for
C18H16N6O 333.1464, found 333.1453.
.
9-Benzyl-8-hydroxy-2-(isopropylamino)adenine (9f). A
colorless solid (59% for three steps from 6), mp 243–
9-Benzyl-2-[(4-fluorobenzyl)amino]-8-hydroxyadenine
(9x). A colorless solid (16% for three steps from 6), mp
246 ꢀC; H NMR (DMSO-d6) d 9.64 (1H, s), 7.34–7.21
1
283–285 ꢀC; H NMR (DMSO-d6) d 9.69 (1H, s), 7.34–
1
(5H, m), 5.99 (2H, s), 5.98 (1H, d, J=8.2 Hz), 4.80 (2H, s),
4.00–3.90 (1H, m), 1.08 (6H, d, J=6.4 Hz); MS (EI) m/z
298 (M+); HRMS calcd for C15H18N6O 298.1542, found
7.20 (7H, m), 7.08–7.02 (2H, m), 6.85 (1H, t, J=6.3 Hz),
6.06 (2H, s), 4.79 (2H, s), 4.36 (2H, d, J=6.3 Hz); MS
(FAB) m/z 365 (MH+); HRMS calcd for C19H18FN6O
.
298.1530. Anal. calcd for C15H18N6O 1/4H2O: C, 59.49;
H, 6.16; N, 27.75. Found: C, 59.45; H, 5.97; N, 27.79.
365.1526,
found
.
365.1536.
Anal.
calcd
for
C19H17FN6O H2O: C, 59.68; H, 5.01; N, 21.98. Found:
C, 59.46; H, 4.90; N, 22.04.
9-Benzyl-8-hydroxy-2-(isobutyllamino)adenine (9g). A
colorless solid (26% for three steps from 6), mp 251–
ꢀ
1
253 C; H NMR (DMSO-d6) d 9.63 (1H, s), 7.30–7.22
(5H, m), 6.24 (1H, t, J=6.0 Hz), 5.99 (2H, s), 4.80
(2H, s), 2.99 (2H, t, J=6.0 Hz), 1.84–1.75 (1H, m),
0.84 (6H, d, J=6.8 Hz); MS (EI) m/z 312 (M+);
HRMS calcd for C16H20N6O 312.1698, found
9-Benzyl-2-(N-benzyl-N-methylamino)-8-hydroxyadenine
(9ab). A colorless solid (54% for three steps from 6),
mp 256–257 ꢀC; H NMR (DMSO-d6) d 9.70 (1H, s),
1
7.29–7.19 (10H, m), 6.12 (2H, s), 4.81 (2H, s), 4.77 (2H,
s), 2.99 (3H, s); MS (EI) m/z 360 (M+); HRMS calcd
for C20H20N6O 360.1698, found 360.1676. Anal. calcd
.
312.1692. Anal. calcd for C16H20N6O 11/10H2O: C,
57.85; H, 6.74; N, 25.30. Found: C, 57.63; H, 6.60; N,
25.50.
.
for C20H20N6O 1/5H2O: C, 65.99; H, 5.65; N, 23.09.
Found: C, 66.08; H, 5.52; N, 23.15.
9-Benzyl-2-(s-butylamino)-8-hydroxyadenine (9h). A col-
orless solid (27% for three steps from 6), mp 234–
9-Benzyl-8-hydroxy-2-(4-methylpiperazin-1-yl)adenine
(9ac). A colorless solid (17% for three steps from 6),
235 ꢀC; H NMR (DMSO-d6) d 9.63 (1H, s), 7.31–7.24
mp 248–250 ꢀC; H NMR (DMSO-d6) d 9.77 (1H, s),
1
1
(5H, m), 5.97 (2H, s), 5.95 (1H, d, J=8.6 Hz), 4.80 (2H,
s), 3.82–3.74 (1H, m), 1.51–1.34 (2H, m), 1.04 (3H, d,
J=6.4 Hz), 0.83 (3H, t, J=7.3 Hz); MS (EI) m/z 312
7.24–7.32 (5H, m), 6.15 (2H, s), 4.82 (2H, s), 3.58 (4H,
s), 2.32–2.27 (4H, m), 2.19 (3H, s); MS (FAB) m/z 340
(MH+); HRMS calcd for C17H22N7O 340.1886, found