HCID 135767963, compound → HCID 136107582, compound

HRID 1757407Notes

Reaction equation

HRID 1757407 reaction equation
[NH2:1][C:2]1[NH:3][C:4](=[O:37])[C:5]2[S:10][C:9](=[O:11])[N:8]([C@@H:12]3[O:25][C@H:24]([CH2:26][O:27]C(=O)C4C=CC=CC=4)[C@@H:14]([O:15]C(=O)C4C=CC=CC=4)[C@@H:13]3[F:36])[C:6]=2[N:7]=1>N.CO.CO>[NH2:1][C:2]1[NH:3][C:4](=[O:37])[C:5]2[S:10][C:9](=[O:11])[N:8]([C@@H:12]3[O:25][C@H:24]([CH2:26][OH:27])[C@@H:14]([OH:15])[C@@H:13]3[F:36])[C:6]=2[N:7]=1

Participants

4

Reactant 1

HCID 135767963HCID 135767963, compound

Product 1

HCID 136107582HCID 136107582, compoundYield 86.9%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 21705897Ammonia methanolSolvent

Procedure

Treatment of 5-amino-3-(2-deoxy-2-fluoro-3,5-di-O-benzoyl-β-D-arabinofuranosyl)thiazolo[4,5-d]pyrimidine-2,7(3H,6H)-dione (0.40 g, 0.76 mmol) in NH3 /MeOH (saturated at 0° C., 35 mL) at room temperature for 24 h gavethe deblocked nucleoside. This was dissolved in MeOH, adsorbed on silica gel (10 g) and loaded on the top of a prepacked silica gel column. The column was eluted with CH2Cl2 :MeOH (90:10, v:v). The appropriate fractions were pooled and concentrated to afford 0.21 g (86.9%) of the title compound, mp 232°-234° C.; Ir (KBr): ν 3200-3450 (OH, NH), 1660 (C=O) and 1677 (C=O) cm-1. Uv, λ max (nm),(ε×10-3): pH 1, 302 (8.4), 242 (8.8), 222 (10.2); pH 7, 302 (8.6), 242 (9.1), 222 (10.3); pH 11, 220 (9.9), 242 (7.6), 294 (6.0); 1H nmr (DMSO-d6): δ 3.65 (t,2 H, C5'H2), 4.23 (m, 1 H, C4'H), 4.55 (tt, 1 H, C3'H), 4.72 (m, 1 H, C3'OH), 5.36 (tt, J2,HF=40.4 Hz, 1 H, C2'H),5.72 (m, 1 H, C5'OH), 6.30 (dd, J1',2' =2.12 Hz, 1 J1'H,F =12.52 Hz, 1 H, C1'H), 6.96 (br s, 2 H, NH2) and 11.25 (br s, 1H, NH); Anal. Calc'd for C10H11OF5S 0.25 CH3OH: C, 37.73; H, 3.71; N, 17.16: S, 9.82; F, 5.82. Found: C, 37.93; H, 3.86; N, 16.72; S, 9.53; F, 5.52.

Workup

  1. washThe column was eluted with CH2Cl2 :MeOH (90:10, v:v)
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-139ca0119b6c4d14a4179acb02724492
Source dataset
uspto-grants-1995_08
Patent number
US05446045

Reaction notes

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