ORDER
REPRINTS
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Abramov et al.
tube, which was tightly sealed with an aluminum/Teflon crimp, was irradiated
at 150 W, 110°C with gas jet cooling for 15 min in a CEM-Discover mono-
mode microwave apparatus. The vessel was cooled down to 60°C and the
residue was powdered into ice-water (10 mL). The pH was adjusted to neutral
with 1N HCl at 0°C and solid formed was filtered off, washed with water, and
dissolved in dichloromethane (50 mL). The solution was dried over
magnesium sulfate, concentrated and crude material was purified by column
chromatography on silica gel (35% yield).
1H NMR: (DMSO-d6, 500 MHz, d): 3.69 (1H, dd, J = 2.4 Hz, J = 9.5 Hz, 4’-H);
3.80 (1H, t, J = 10.2 Hz, 6’ax-H), 4.00 (1H, td, J = 5.1 Hz, J = 10.2 Hz, 5’-
H); 4.23–4.30 (4H, m, 1’eq-H, 1’ax-H, 3’-H, and 6’eq-H); 4.46 (1H, br s, 2’-
H); 5.64 (1H, s, PhCH); 5.88 (1H, d, J = 4.5 Hz, 3’-OH), 6.98 (2H, s, NH2);
7.32–7.34 (3H, m, H arom); 7.38–7.40 (2H, m, H arom); 8.23 (1H, s, 8–11).
13C NMR: (DMSO-d6, 125 MHz, d): 55.87 (2’-C); 64.29 (1’-C); 64.77 (3’-C);
66.46 (5’-C); 68.13 (6’-C); 76.27 (4’-C); 101.06 (PhCH); 123.02 (5-C);
126.41-137.75 (4 ꢁ C arom); 141.37 (8-C); 149.73 (2-C); 154.26 (4-C);
159.93 (6-C).
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HRMS: calcd for C18H19ClN5O4(M + H) 404.1125, found 404.1119.
c) When epoxidation of 2-amino-6-chloropurin was carried out in DMF the
formation of next by-products have been observed.
2-(2-Amino-6-N,N-dimethylaminopurin-9-yl)-1,5-anhydro-4,6-O-benzylidene-2-
deoxy-D-altro-hexitol. Yield 25% (18). 1H NMR: (DMSO-d6, 500 MHz, d): 3.57 (6H,
br s, N(CH3)2); 3.67 (1H, dd, J = 2.4 Hz, J = 9.5 Hz, 4’-H); 3.77 (1H, t, J = 10.2 Hz,
6’ax-H), 3.99 (1H, td, J = 5.1 Hz, J = 10.2 Hz, 5’-H); 4.16–4.29 (4H, m, 1’eq-H, 1’ax-H,
3’-H, and 6’eq-H); 4.39 (1H, br s, 2’-H); 5.64 (1H, s, PhCH); 5.80 (1H, br s, 3’-OH), 5.88
(2H, s, NH2); 7.32–7.34 (3H, m, H arom); 7.40–7.42 (2H, m, H arom); 7.92 (1H, s,8-H).
13C NMR: (DMSO-d6, 125 MHz, d): 37.70 (N(CH3)2); 55.16 (2’-C); 64.59 (1’-C);
64.96 (3’-C); 66.34 (5’-C); 68.21 (6’-C); 76.42 (4’-C); 101.06 (PhCH); 113.24 (5-C);
126.41–137.75 (4 ꢁ C arom); 134.74 (8-C); 152.87 (4-C); 154.88 (4-C) and 159.66 (2-C
and 6-C).
HRMS: calcd for C20H25N6O4(M + H)+ 413.1937, found 413.1916.
2-(2-Amino-6-chloropurin-7-yl)-1,5-anhydro-4,6-O-benzylidene-2-deoxy-D-
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altro-hexitol (19). Yield 5%. 1H NMR: H NMR: (DMSO-d6, 500 MHz, d): 3.62
(1H, dd, J = 2.4 Hz, J = 9.5 Hz, 4’-H); 3.78 (1H, t, J = 10.2 Hz, 6’ax-H), 3.99 (1H, td,
J = 5.1 Hz, J = 10.2 Hz, 5’-H); 4.24–4.38 (4H, m, 1’eq-H, 1’ax-H, 3’-H, and 6’eq-H);
4.74 (1H, br s, 2’-H); 5.61 (1H, s, PhCH); 6.00 (1H, d, J = 4.4 Hz, 3’-OH), 6.65 (2H, s,
NH2); 7.32–7.34 (3H, m, H arom); 7.38–7.40 (2H, m, H arom); 8.46 (1H, s, 8-H).
13C NMR: (DMSO-d6, 125 MHz, d): 57.90 (2’-C); 64.45 (1’-C); 66.23 (3’-C);
66.50 (5’-C); 68.11 (6’-C); 75.69 (4’-C); 101.00 (PhCH); 115.22 (5-C); 126.35–137.77
(4 ꢁ C arom); 142.49 (8-C); 147.54 (2-C); 160.11 (6-C); 163.86 (4-C).
HRMS: calcd for C18H19ClN5O4(M + H)+ 404.1125, found 404.1119.
[2-Amino-6-(2-amino-6-chloropurin)purin-9-yl]-1,5-anhydro-4,6-O-benzyli-
dene-2-deoxy-D-altro-hexitol (20). Yield 5%. 1H NMR: (DMSO-d6, 500 MHz,