Chemical Papers
201–202 °C. IR (KBr): 3332, 3109, 3010, 2929, 2875, 1595,
J=3.7, 10.2 Hz, 1H, NCHAHB), 4.38–4.44 (m, 1H, CHOH),
4.47 (s, 1H, OH, exchangeable with D2O), 4.60–4.65 (m,
2H, OCH2), 7.14 (br s, 2H, NH2, exchangeable with D2O),
7.45–7.51 (m, 5H, aryl), 8.30 (s, 1H, C(2)–H of adenine),
8.42 (s, 1H, C(8)–H of adenine). 13C NMR (DMSO-d6,
62.5 MHz) δppm = 46.72, 69.48, 70.07, 114.64, 119.09,
121.11, 129.85, 141.92, 150.05, 152.76, 156.32, 158.56.
MS (EI): m/z (%) = 285 (14.6) [M+]. Anal. Calc. for
C14H15N5O2: C, 58.94; H, 5.30; N, 24.55; found: C, 59.03;
H, 5.21; N, 24.67.
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1487, 1242, 1047 cm−1; H NMR (DMSO-d6, 250 MHz)
δppm =3.81 (s, 2H, NH2, exchangeable with D2O), 4.29 (t,
J=4.9 Hz, 2H, NCH2), 4.49 (t, J=4.9 Hz, 2H, OCH2), 6.82
(s, 2H, PhCH2), 7.05–7.25 (complex, 10 H, aryl, C(2)–H
of adenine), 8.14 (s, 1H, C(8)–H of adenine). 13C NMR
(DMSO-d6, 62.5 MHz) δppm =40.11, 42.48, 65.58, 114.43,
118.58, 125.76, 128.29, 128.48, 129.64, 133.72, 141.10,
141.56, 149.47, 152.40, 155.90, 156.18. MS (EI): m/z
(%)=345 (15.3) [M+]. Anal. Calc. for C20H19N5O: C, 69.55;
H, 5.54; N, 20.28; found: C, 69.38; H, 5.70; N, 20.07.
6‑Chloro‑9‑(4‑(4‑chlorophenoxy)butyl)‑9H‑purine (entry 9)
9‑(Hex‑5‑enyl)‑9H‑purin‑6‑amine (entry 6, Soltani Rad et al.
Column chromatography on silica gel eluted with hex-
ane/EtOAc (2:1) afforded pure product as white solid
(2.73 g, 81%); m.p. 110–111 °C. IR (KBr): 3095, 2947,
2873, 1591, 1473, 1238, 1045 cm−1. 1H NMR (DMSO-d6,
250 MHz) δppm =1.61–1.72 (m, 2H, NCH2CH2), 1.94–2.05
(m, 2H, OCH2CH2), 3.91 (t, J = 6.3 Hz, 2H, NCH2), 4.34
(t, J = 7.0 Hz, 2H, OCH2), 6.83–6.89 (complex, 3H, aryl,
C(2)–H of purine), 7.21–7.27 (m, 2H, aryl), 8.69 (s, 1H,
C(8)–H of purine). 13C NMR (DMSO-d6, 62.5 MHz)
δppm =25.65, 25.78, 43.53, 67.07, 116.04, 124.07, 129.06,
130.78, 147.41, 148.91, 151.33, 151.88, 157.21. MS (EI):
m/z (%)=336 (30.8) [M+]. Anal. Calc. for C15H14Cl2N4O:
C, 53.43; H, 4.18; N, 16.62; found: C, 53.28; H, 4.34; N,
16.53.
Column chromatography on silica gel eluted with EtOAc
aforded pure product as white solid (1.74 g, 80%); m.p.
140–141 °C. IR (KBr): 3330, 3115, 2948, 1489 cm−1. H
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NMR (DMSO-d6, 250 MHz) δppm =1.31–1.40 (m, 2H, CH2),
1.81-1.90 (m, 2H, CH2), 2.03–2.09 (m, 2H, CH2), 4.20 (t,
J=7.0 Hz, 2H, NCH2), 4.93 (dd, J=1.3, 9.2 Hz, 2H,=CH2),
5.69–5.78 (m, 1H, =CH), 7.32 (br. s, 2H, NH2, exchange-
able with D2O), 8.22 (s, 1H, C(2)–H of adenine), 8.25 (s,
1H, C(8)–H of adenine). 13C NMR (DMSO-d6, 62.5 MHz)
δppm =25.18, 29.07, 32.45, 42.64, 114.85, 118.68, 138.15,
140.76, 149.48, 152.31, 155.90. MS (EI): m/z (%)=217 (21)
[M+]. Anal. Calc. for C11H15N5: C, 60.81; H, 6.96; N, 32.23;
found: C, 60.96; H, 7.08; N, 32.35.
7‑Allyl‑1,3‑dimethyl‑1H‑purine‑2,6(3H,7H)‑dione (entry 10,
(E)‑9‑Cinnamyl‑9H‑purin‑6‑amine (entry 7, Soltani Rad
Soltani Rad et al. 2009b)
Column chromatography on silica gel eluted with hexane/
EtOAc (1:1) aforded pure product as white solid (2.09 g,
95%); m.p. 103–104 °C. IR (KBr): 3050, 2987, 2890,
Column chromatography on silica gel eluted with EtOAc
aforded pure product as yellow solid (2.11 g, 84%); m.p.
237–238 °C. IR (KBr): 3355, 3130, 2950, 1492, 1453 cm−1.
1H NMR (DMSO-d6, 250 MHz) δppm =4.93 (d, J=5.0 Hz,
2H, NCH2), 6.43 (d, J = 16.4 Hz, 1H, PhCH), 7.21–7.31
(complex, 6H, NCH2CH, aryl), 7.37 (s, 1H, C(2)–H of ade-
nine), 7.40 (s, 2H, NH2, exchangeable with D2O), 8.15 (s,
1H, C(8)–H of adenine). 13C NMR (DMSO-d6, 62.5 MHz)
δppm = 44.50, 118.63, 124.56, 126.38, 127.85, 128.57,
132.31, 135.80, 140.58, 149.35, 152.49, 155.93. MS (EI):
m/z (%) = 251 (29.8) [M+]. Anal. Calc. for C14H13N5: C,
66.92; H, 5.21; N, 27.87; found: C, 66.81; H, 5.36; N, 27.96.
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1725, 1708, 1473 cm−1. H NMR (DMSO-d6, 250 MHz)
δppm = 3.17 (s, 3H, N(3)–CH3), 3.36 (s, 3H, N(1)–CH3),
4.73 (d, J = 5.2 Hz, 2H, NCH2), 5.00–5.13 (dd, J = 11.5,
16.4 Hz, 2H,=CH2), 5.77–5.93 (m, 1H,=CH), 7.40 (s, 1H,
C(8)–H of theophylline). 13C NMR (DMSO-d6, 62.5 MHz)
δppm =27.80, 29.61, 48.83, 106.71, 119.18, 132.06, 140.71,
148.64, 151.50, 154.95. MS (EI): m/z (%)=220 (25.4) [M+].
Anal. Calc. for C10H12N4O2: C, 54.54; H, 5.49; N, 25.44;
found: C, 54.68; H, 5.57; N, 25.32.
7‑Benzyl‑1, 3‑dimethyl‑1H‑purine‑2,6 (3H,7H)‑dione (entry
11, Soltani Rad et al. 2009b)
1‑(6‑Amino‑9H‑purin‑9‑yl)‑3‑phenoxypropan‑2‑ol (entry 8,
Column chromatography on silica gel eluted with hexane/
EtOAc (1:1) aforded pure product as white solid (2.51 g,
93%); m.p. 158–159 °C. IR (KBr): 3100, 2980, 2895,
Column chromatography on silica gel eluted with hexane/
EtOAc (2:1) aforded pure product as white solid (2.25 g,
79%); m.p. 137–138 °C. IR (KBr): 3500, 3350, 3090,
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1720, 1705, 1471 cm−1. H NMR (DMSO-d6, 250 MHz)
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2974, 1467, 1238 cm−1. H NMR (DMSO-d6, 250 MHz)
δppm = 3.31 (s, 3H, N(3)–CH3), 3.49 (s, 3H, N(1)–CH3),
δppm = 4.14 (dd, J = 6.2, 10.2 Hz, H, NCHAHB), 4.30 (dd,
5.42 (s, 2H, NCH2), 7.12–7.31 (m, 5H, aryl), 7.54 (s, 1H,
1 3