E. Vanotti et al. / Tetrahedron 58 (2002) 3361±3370
3367
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1700; 1650; 1570; 1520; 1440; 1380; 775; 750. H NMR
(400 MHz, DMSO-d6): d 5.38 (2H, s), 5.66 (2H, s), 6.74
(2H, br. s), 7.36 (1H, dd, J8.5, 1.7 Hz), 7.46±7.53 (5H, m),
7.62 (1H, s), 7.75±7.90 (7H, m), 8.23 (1H, s); 13C NMR
(100 MHz, DMSO-d6): d 43.4 (1C), 49.4 (1C), 107.2 (1C),
124±128 (14C), 132±135 (6C), 144.1 (1C), 153.1 (1C),
154.4 (1C), 158.2 (1C); MS m/z 432 [M1H]1; Anal.
calcd for C27H21N5O: C, 75.16; H, 4.91; N, 16.23. Found:
C, 74.85; H, 4.98; N, 15.94.
(1H, t, J7 Hz), 7.75 (1H, s), 7.8±7.97 (5H, m), 8.22 (1H,
s), 8.35 (1H, d, J8.5 Hz); MS m/z 433 [M1H]1; Anal.
calcd for C26H20N6O: C, 72.21; H, 4.66; N, 19.43. Found:
C, 71.84; H, 4.71; N, 19.15.
4.1.24. 2-Amino-3-(2,1,3-benzoxadiazol-5-ylmethyl)-7-
(2-naphthylmethyl)-3,7-dihydro-6H-purin-6-one (24).
1
Yield: 29%, white solid, mp.3008C; H NMR (400 MHz,
DMSO-d6): d 5.44 (2H, s), 5.71 (2H, s), 7.07 (2H, br. s),
7.5±7.6 (4H, m), 7.69 (1H, s), 7.85±7.9 (4H, m), 8.06 (1H,
d, J9.4 Hz), 8.14 (1H, s); MS m/z 424 [M1H]1; Anal.
calcd for C23H17N7O2: C, 65.24; H, 4.05; N, 23.15. Found:
C, 65.31; H, 4.24; N, 22.76.
With this procedure and starting from the convenient 7-aryl-
methylguanine hydrochlorides and (hetero)arylmethyl
halides the following compounds were prepared.
4.1.18. 2-Amino-3-(3,4-dichlorobenzyl)-7-(2-naphthyl-
methyl)-3,7-dihydro-6H-purin-6-one (18). Yield 26%,
whitish solid, mp 235±2388C; 1H NMR (400 MHz,
DMSO-d6): d 5.28 (2H, s), 5.67 (2H, s), 7.0 (2H, br. s),
7.14 (1H, dd, J8.3, 2.2 Hz), 7.47±7.57 (5H, m), 7.82±
7.90 (4H, m), 8.11 (1H, s); MS m/z 450 [M1H]1; Anal.
calcd for C23H17Cl2N5O: C, 61.35; H, 3.81; N, 15.55.
Found: C, 61.24; H, 3.88; N, 15.32.
4.1.25. 2-Amino-1-(2,1,3-benzoxadiazol-5-ylmethyl)-7-
(2-naphthylmethyl)-1,7-dihydro-6H-purin-6-one (25).
Yield: 22%, whitish solid, mp 284±2868C; 1H NMR
(400 MHz, DMSO-d6): d 5.33 (2H, s), 5.64 (2H, s), 6.82
(2H, br. s), 7.44±7.51 (4H, m), 7.62 (1H, s), 7.79 (1H, s),
7.89±7.90 (3H, m), 8.01 (1H, d, J9.3 Hz), 8.24 (1H, s);
MS m/z 424 [M1H]1; Anal. calcd for C23H17N7O2: C,
65.24; H, 4.05; N, 23.15. Found: C, 64.89; H, 4.14; N, 22.75.
4.1.19. 2-Amino-1-(3,4-dichlorobenzyl)-7-(2-naphthyl-
methyl)-1,7-dihydro-6H-purin-6-one (19). Yield: 15%,
4.1.26.
2-Amino-3-(1,3-benzodioxol-5-ylmethyl)-7-(2-
naphthylmethyl)-3,7-dihydro-6H-purin-6-one (26). Yield:
33%, whitish solid, mp.2808C; 1H NMR (400 MHz,
DMSO-d6): d 5.21 (2H, s), 5.69 (2H, s), 5.97 (2H, s), 6.77
(1H, dd, J7.9, 1.3 Hz), 6.84 (1H, d, J7.9 Hz), 6.87 (1H, d,
J1.3 Hz), -6.95 (2H, br. s), 7.52 (2H, m), 7.54 (1H, dd,
J8.5, 1.5 Hz), 7.85±7.9 (4H, m), 8.13 (1H, s); MS m/z
426 [M1H]1; Anal. calcd for C24H19N5O3: C, 67.76; H,
4.50; N, 16.46. Found: C, 67.41; H, 4.58; N, 16.21.
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white solid, mp 212±2138C; H NMR (400 MHz, DMSO-
d6): d 5.21 (2H, s), 5.6 (2H, s), 6.87 (2H, br. s), 7.3±7.9
(10H, m), 8.24 (1H, s); MS m/z 450 [M1H]1; Anal. calcd
for C23H17Cl2N5O: C, 61.35; H, 3.81; N, 15.55. Found: C,
61.38; H, 4.11; N, 15.12.
4.1.20. 2-Amino-7-(2-naphthylmethyl)-3-(3-phenoxy-
benzyl)-3,7-dihydro-6H-purin-6-one (20). Yield: 33%,
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white solid, mp 220±2268C; H NMR (400 MHz, DMSO-
4.1.27.
2-Amino-1-(1,3-benzodioxol-5-ylmethyl)-7-(2-
d6): d 5.34 (2H, s), 5.69 (2H, s), 6.87 (1H, dd, J7.8,
1.7 Hz), 6.95±7.0 (4H, m), 7.12 (1H, t, J7.7 Hz), 7.3±
7.4 (3H, m), 7.41 (2H, br. s), 7.50±7.55 (3H, m), 7.85±7.9
(4H, m), 8.21 (1H, s); MS m/z 474 [M1H]1; Anal. calcd for
C29H23N5O2: C, 73.56; H, 4.90; N, 14.79. Found: C, 73.35;
H, 5.04; N, 14.59.
naphthylmethyl)-1,7-dihydro-6H-purin-6-one (27). Yield:
12%, white solid, mp 258±2638C; 1H NMR (400 MHz,
DMSO-d6): d 5.19 (2H, s), 5.61 (2H, s), 5.94 (2H, s), 6.75
(1H, dd, J7.7, 1.2 Hz), 6.85 (1H, d, J7.7 Hz), 6.89 (2H, br.
s), 6.93 (1H, d, J1.2 Hz), 7.5±7.9 (7H, m), 8.22 (1H, s); MS
m/z 426 [M1H]1; Anal. calcd for C24H19N5O3: C, 67.76; H,
4.50; N, 16.46. Found: C, 67.61; H, 4.72; N, 16.01.
4.1.21.
2-Amino-7-(2-naphthylmethyl)-1-(3-phenoxy-
benzyl)-1,7-dihydro-6H-purin-6-one (21). Yield: 20%,
whitish solid, mp 218±2228C; 1H NMR (400 MHz,
DMSO-d6): d 5.25 (2H, s), 5.61 (2H, s), 6.8±7.8 (18H,
m), 8.29 (1H, s); MS m/z 474 [M1H]1; Anal. calcd for
C29H23N5O2: C, 73.56; H, 4.90; N, 14.79. Found: C,
73.20; H, 4.94; N, 14.72.
4.1.28. 2-Amino-7-(2-naphthylmethyl)-3-(4-nitrobenzyl)-
3,7-dihydro-6H-purin-6-one (28). Yield: 37%, whitish
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solid, mp 268±2698C; H NMR (400 MHz, DMSO-d6): d
5.46 (2H, s), 5.70 (2H, s), 7.05 (2H, br. s), 7.46 (2H, d,
J8.8 Hz), 7.5±7.6 (3H, m), 7.87±7.91 (4H, m), 8.12
(1H, s), 8.20 (2H, d, J8.8 Hz); MS m/z 427 [M1H]1;
Anal. calcd for C23H18N6O3: C, 64.78; H, 4.25; N, 19.71.
Found: C, 64.91; H, 4.51; N, 19.41.
4.1.22. 2-Amino-7-(2-naphthylmethyl)-3-(2-quinolinyl-
methyl)-3,7-dihydro-6H-purin-6-one (22). Yield: 31%,
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white solid, mp 285±2868C; H NMR (400 MHz, DMSO-
4.1.29. 2-Amino-7-(2-naphthylmethyl)-1-(4-nitrobenzyl)-
1,7-dihydro-6H-purin-6-one (29). Yield: 33%, white solid,
mp.2858C; 1H NMR (400 MHz, DMSO-d6): d 5.34 (2H, s),
5.63 (2H, s), 6.8 (2H, br. s), 7.4 (2H, d, J8.7 Hz), 7.47 (1H,
dd, J8.5, 1.7 Hz), 7.51 (2H, m), 7.77 (1H, s), 7.85±7.9
(3H, m), 8.16 (2H, d, J8.7 Hz), 8.24 (1H, s); MS m/z
427 [M1H]1; Anal. calcd for C23H18N6O3: C, 64.78; H,
4.25; N, 19.71. Found: C, 64.44; H, 4.35; N, 19.36.
d6): d 5.59 (2H, s), 5.7 (2H, s), 6.99 (2H, br. s), 7.37 (1H, d,
J8.5 Hz), 7.5±7.75 (5H, m), 7.85±7.97 (6H, m), 8.06 (1H,
s), 8.35 (1H, d, J8.5 Hz); MS m/z 433 [M1H]1; Anal.
calcd for C26H20N6O: C, 72.21; H, 4.66; N, 19.43. Found:
C, 71.80; H, 4.73; N, 19.4.
4.1.23. 2-Amino-7-(2-naphthylmethyl)-1-(2-quinolinyl-
methyl)-1,7-dihydro-6H-purin-6-one (23). Yield: 25%,
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white solid, mp 265±2698C; H NMR (400 MHz, DMSO-
4.1.30. 2-Amino-3-(3,4-di¯uorobenzyl)-7-(2-naphthyl-
methyl)-3,7-dihydro-6H-purin-6-one (30). Yield: 28%,
white solid, mp 236±2378C; 1H NMR (400 MHz,
d6): d 5.46 (2H, s), 5.63 (2H, s), 6.77 (2H, br. s), 7.39 (1H, d,
J8.5 Hz), 7.46±7.51 (3H, m), 7.59 (1H, t, J7 Hz), 7.73