832
V. Kumar and S. V. Malhotra
69.25 (C4ꢁ), 60.80 (C5ꢁ), 40.13 (C2ꢁ); LC-MS (ESI-TOF): m/z 354.995241
([M+H]+, C9H12IN2O5 calcd. 354.97854).
5-Bromo-2ꢁ-deoxyuridine (4b):[11] Obtained as white solid with m.p.
1
174–176◦C (dec) (lit. m.p. 175–179◦C (dec)[11]); H NMR (400 MHz,
DMSO-d6, δ) δ 11.76 (s, 1H, NH), 8.36 (s, 1H, H6), 6.07 (t, 1H, J = 6.5
Hz, H1ꢁ), 5.22 (brs, 1H, OH3ꢁ), 5.14 (brs, 1H, OH5ꢁ), 4.21 (d, 1H, J =
3.3 Hz, H3ꢁ), 3.77 (q, 1H, J = 3.2 Hz, H4ꢁ), 3.57 (dd, 2H, J = 11.7 and
25.3 Hz, H5ꢁ), 2.19–2.01 (m, 2H, H2ꢁ). 13C NMR (101 MHz, DMSO-d6, δ)
159.17 (C4), 149.74 (C2), 140.27 (C6), 95.66 (C5), 87.57 (C1ꢁ), 84.86 (C3ꢁ),
69.96 (C4ꢁ), 60.79 (C5ꢁ), 40.13 (C2ꢁ); LC-MS (ESI-TOF): m/z 307.00631
([M+H]+, C9H12BrN2O5 calcd. 306.99241).
5-Chloro-2ꢁ-deoxyuridine (4c):[11] Obtained as white solid with m.p.
1
174–178◦C (dec) (lit. m.p. 173–176◦C (dec)[11]); H NMR (400 MHz,
DMSO-d6, δ) 11.80 (brs, 1H, NH), 8.28 (s, 1H, H6), 6.08 (t, 1H, J = 6.5
Hz, H1ꢁ), 5.22 (d, 1H, J = 3.8 Hz, OH3ꢁ), 5.14 (brs, 1H, OH5ꢁ), 4.21 (brs,
1H, H3ꢁ), 3.77 (q, 1H, J = 3.2 Hz, H4ꢁ), 3.52–3.62 (m, 2H, H5ꢁ), 2.15–2.03
(m, 2H, H2ꢁ). 13C NMR (101 MHz, DMSO-d6, δ) 160.09 (C4), 150.40 (C2),
137.39 (C6), 107.27 (C5), 87.45 (C1ꢁ), 84.76 (C3ꢁ), 70.02 (C4ꢁ), 60.89 (C5ꢁ),
40.09 (C2ꢁ); LC-MS (ESI-TOF): m/z 263.05489 ([M+H]+, C9H12ClN2O6
calcd. 263.04293).
5-Iodouridine (4d):[11] Obtained as white solid with m.p. 205–210◦C
1
(dec) (lit. m.p. 207–209◦C (dec)[11]); H NMR (400 MHz, DMSO-d6, δ)
11.68 (s, 1H, NH), 8.48 (s, 1H, H6), 5.72 (d, 1H, J = 4.6 Hz, H1ꢁ), 5.41 (d,
1H, J = 5.0 Hz, OH3ꢁ), 5.26 (t, 1H, J = 4.5 Hz, OH5ꢁ), 5.07 (d, 1H, J = 5.0
Hz, OH2ꢁ), 4.01 (dq, 2H, J = 4.6 and 21.6 Hz, H3ꢁ and H2ꢁ), 3.87 (dt, 1H, J =
2.6 and 4.9 Hz, H4ꢁ), 3.73–3.64 (m, 1H,a H5ꢁ), 3.62–3.53 (m, 1H,b H5ꢁ). 13
C
NMR (101 MHz, DMSO-d6, δ) 160.48 (C4), 150.35 (C2), 145.11 (C6), 96.17
(C5), 88.27 (C1ꢁ), 84.73 (C3ꢁ), 73.95 (C2ꢁ), 69.31 (C4ꢁ), 60.18 (C5ꢁ); LC-MS
(ESI-TOF): m/z 370.99221 ([M+H]+, C9H12IN2O6 calcd. 370.97346).
5-Bromouridine (4e):[11] Obtained as white solid with m.p. 190–95◦C
1
(dec) (lit. m.p. 190–198◦C (dec)[11]); H NMR (400 MHz, DMSO-d6, δ)
δ11.78 (s, 1H, NH), 8.45 (s, 1H, H6), 5.70 (d, 1H, J = 4.5 Hz, H1ꢁ), 5.40
(d, 1H, J = 5.2 Hz, OH3ꢁ), 5.25 (t, 1H, J = 4.7 Hz, OH5ꢁ), 5.04 (d, 1H,
J = 4.6 Hz, OH2ꢁ), 4.01 (dd, 1H, J = 4.7 and 9.4 Hz, H3ꢁ), 3.96 (d, 1H, J
= 4.2 Hz, H2ꢁ), 3.84 (dt, 1H, J = 2.7 and 4.9 Hz), 3.67 (dd, 1H, J = 6.7
and 9.8 Hz), 3.59–3.50 (m, 1H). 13C NMR (101 MHz, DMSO-d6, δ)159.14
(C4), 149.97 (C2), 140.35 (C6), 95.69 (C5), 88.49 (C1ꢁ), 84.67 (C3ꢁ), 73.94
(C2ꢁ), 69.25 (C4ꢁ), 60.11 (C5ꢁ); LC-MS (ESI-TOF): m/z 323.0019 ([M+H]+,
C9H12BrN2O6 calcd. 322.98733).
5-Chlorouridine (4f):[11] Obtained as white solid with m.p. 210–216◦C
1
(dec) (lit. m.p. 215–220◦C (dec)[11]); H NMR (400 MHz, DMSO-d6, δ)
11.85 (s, 1H, NH), 8.41 (s, 1H, H6), 5.73 (d, 1H, J = 4.5 Hz, H1ꢁ), 5.43
(d, 1H, J = 5.3 Hz, OH3ꢁ), 5.28 (t, 1H, J = 4.7 Hz, OH5ꢁ), 5.08 (d, 1H, J =