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Helvetica Chimica Acta – Vol. 98 (2015)
2-({1-[3-(2,4-Dichlorophenoxy)-2-hydroxypropyl]-1H-1,2,3-triazol-4-yl}methyl)-1,2,4-triazine-
3,5(2H,4H)-dione (3e). Yield: 3.34 g (81%; CC (SiO2; AcOEt)). White solid. M.p. 202 – 2038. IR (KBr):
3345 (br.), 3100s, 2971m, 1720s, 1705s, 1663m, 1459s, 1215s, 775s. 1H-NMR ((D6)DMSO): 12.54 (s, NH,
exchangeable with D2O); 7.88 (s, HÀC(5) of triazol); 7.42 (s, HÀC(5) of azauracil, 1 arom. H); 7.25 – 7.20
(m, 1 arom. H); 7.05 (d, J ¼ 7.5, 1 arom. H); 5.50 (s, OH, exchangeable with D2O); 4.87 (s, NCH2C¼C);
4.49 – 4.26 (m, CHOH, CH2O); 3.95 – 3.84 (m, NCH2CH). 13C-NMR ((D6)DMSO): 155.84; 152.77;
148.81; 141.30; 134.70; 129.20; 128.03; 124.68; 124.55; 122.46; 115.17; 70.64; 67.52; 52.47; 34.40. MS: 413
(15.7, Mþ). Anal. calc. for C15H14Cl2N6O4 (413.22): C 43.60, H 3.41, Cl 17.16, N 20.34; found: C 43.67, H
3.35, Cl 17.24, N 20.29.
3,7-Dihydro-7-({1-[2-hydroxy-3-(4-methylphenoxy)propyl]-1H-1,2,3-triazol-4-yl}methyl)-1,3-di-
methyl-1H-purine-2,6-dione (3f). Yield: 3.95 g (93%; CC (SiO2; AcOEt)). Colorless solid. M.p. 116 –
1
1178. IR (KBr): 3250 (br.), 3100s, 2945m, 1723s, 1711s, 1657m, 1461s, 1223s. H-NMR ((D6)DMSO):
8.02 (s, HÀC(8) of theophenyl); 7.97 (s, HÀC(5) of triazol); 6.91 (d, J ¼ 8.2, 2 arom. H); 6.65 (d, J ¼ 8.2, 2
arom. H); 5.43 (s, NCH2C¼C); 4.61 – 4.41 (m, CH2O); 4.34 – 4.25 (m, CHOH); 4.09 (br. s, OH,
exchangeable with D2O); 3.79 – 3.72 (m, NCH2CH); 3.32 (s, MeÀN(1)); 3.24 (s, MeÀN(3)); 2.07 (s,
ArÀMe). 13C-NMR ((D6)DMSO): 162.23; 156.08; 154.30; 150.83; 148.15; 134.47; 133.00; 129.37; 124.76;
114.15; 105.70; 69.36; 67.73; 52.67; 41.02; 29.25; 27.39; 19.92. MS: 425 (9.5, Mþ). Anal. calc. for
C20H23N7O4 (425.45): C 56.46, H 5.45, N 23.05; found: C 56.40, H 5.41, N 23.14.
3,7-Dihydro-7-({1-[2-hydroxy-3-(4-methoxyphenoxy)propyl]-1H-1,2,3-triazol-4-yl}methyl)-1,3-di-
methyl-1H-purine-2,6-dione (3g). Yield: 3.97 g (90%; CC (SiO2; AcOEt)). Colorless solid. M.p. 183 –
1
1848. IR (KBr): 3222 (br.), 3127s, 2931m, 1725s, 1710s, 1657m, 1439s, 1236s. H-NMR ((D6)DMSO):
8.13 (s, HÀC(8) of theophenyl); 8.07 (s, HÀC(5) of triazol); 6.83 – 6.75 (m, 4 arom. H); 5.54 (s,
NCH2C¼C); 5.51 – 5.49 (m, CHOH); 4.51 (dd, J ¼ 13.8, 3.3, 1 H of CH2O); 4.35 (dd, J ¼ 13.8, 7.5, 1 H of
CH2O); 4.15 (s, OH, exchangeable with D2O); 3.83 – 3.80 (m, NCH2CH); 3.65 (s, MeO); 3.35 (s,
MeÀN(1)); 3.16 (s, MeÀN(3)). 13C-NMR ((D6)DMSO): 154.29; 153.43; 152.22; 150.85; 148.17; 142.27;
141.99; 124.77; 115.31; 114.40; 105.72; 69.96; 67.75; 55.21; 52.68; 41.04; 29.28; 27.42. MS: 441 (10.3, Mþ).
Anal. calc. for C20H23N7O5 (441.45): C 54.42, H 5.25, N 22.21; found: C 54.31, H 5.39, N 22.27.
3,7-Dihydro-7-{[1-(2-hydroxyethyl)-1H-1,2,3-triazol-4-yl]methyl}-1,3-dimethyl-1H-purine-2,6-dione
(3h). Yield: 2.86 g (94%; CC (SiO2; AcOEt/hexane 10 :1)). Colorless solid. M.p. 186 – 1878. IR (KBr):
3248 (br.), 3064s, 2952m, 1718s, 1706s, 1668m, 1449s. 1H-NMR (CDCl3): 8.19 (s, HÀC(8) of theophenyl);
8.09 (s, HÀC(5) of triazol); 5.59 (s, NCH2C¼C); 4.38 (t, J ¼ 5.2, CH2O); 3.77 (t, J ¼ 5.2, NCH2CH2); 3.43
(s, MeÀN(1)); 3.39 (s, OH, exchangeable with D2O); 3.24 (s, MeÀN(3)). 13C-NMR (CDCl3): 159.23;
154.41; 152.16; 148.63; 143.15; 122.54; 108.09; 63.37; 56.51; 49.53; 33.48; 29.88. MS: 305 (11.6, Mþ). Anal.
calc. for C12H15N7O3 (305.30): C 47.21, H 4.95, N 32.12; found: C 47.34, H 5.03, N 32.08.
3,7-Dihydro-1-{[1-(2-hydroxyethyl)-1H-1,2,3-triazol-4-yl]methyl}-3,7-dimethyl-1H-purine-2,6-dione
(3i). Yield: 2.44 g (80%; CC (SiO2; AcOEt/MeOH 7:1)). Colorless solid. M.p. 212 – 2138. IR (KBr):
3300 (br.), 3058s, 2947m, 1720s, 1708s, 1661m, 1469s. 1H-NMR ((D6)DMSO): 8.04 (s, HÀC(8) of
theobromin); 7.94 (s, HÀC(5) of triazol); 5.12 (s, NCH2C¼C); 5.05 (s, OH, exchangeable with D2O); 4.35
(t, J ¼ 5.2, CH2O); 3.90 (s, MeÀN(7)); 3.76 (t, J ¼ 5.2, NCH2CH2); 3.43 (s, MeÀN(3)). 13C-NMR
((D6)DMSO): 155.29; 151.72; 150.80; 146.02; 143.58; 123.59; 106.59; 58.78; 56.39; 43.52; 31.28; 30.68.
MS: 305 (14.9, Mþ). Anal. calc. for C12H15N7O3 (305.30): C 47.21, H 4.95, N 32.12; found: C 47.31, H 4.90,
N 32.17.
2-{4-[(6-Amino-9H-purin-9-yl)methyl]-1H-1,2,3-triazol-1-yl}ethanol (3j). Yield: 2.13 g (82%; CC
(SiO2; AcOEt/MeOH 1:4)). Gray solid. M.p. > 2808 (dec.). IR (KBr): 3310 (br.), 3075s, 2981m, 1667m,
1458s. 1H-NMR ((D6)DMSO): 8.18 (s, HÀC(8) of adenine); 7.91 (s, HÀC(5) of triazol); 7.78 (s, HÀC(2) of
adenine); 7.21 (s, NH2, exchangeable with D2O); 4.65 (s, NCH2C¼C); 4.34 (t, J ¼ 7.0, CH2O); 4.16 (s, OH,
exchangeable with D2O); 3.78 (t, J ¼ 7.0, NCH2CH2). 13C-NMR ((D6)DMSO): 160.82; 153.63; 149.75;
144.96; 141.95; 124.60; 120.73; 60.87; 59.68; 58.49. MS: 260 (17.4, Mþ). Anal. calc. for C10H12N8O (260.26):
C 46.15, H 4.65, N 43.06; found: C 46.21, H 4.74, N 43.15.
3-{4-[(6-Amino-9H-purin-9-yl)methyl]-1H-1,2,3-triazol-1-yl}propan-1-ol (3k). Yield: 2.33 g (85%;
CC (SiO2; AcOEt/MeOH 1:4)). Gray solid. M.p. >3108 (dec.). IR (KBr): 3300 (br.), 3040s, 2973m,
1665m, 1462s. 1H-NMR ((D6)DMSO): 8.25 (s, HÀC(8) of adenine); 8.22 (s, HÀC(5) of triazol); 8.12 (s,
HÀC(2) of adenine); 7.32 (s, NH2, exchangeable with D2O); 4.96 (s, NCH2C¼C); 4.62 (s, OH,