Acetic Acid → HCID 11623838, compound

HRID 227441Notes

Reaction equation

HRID 227441 reaction equation
[NH2:1][C:2]1[NH:3][C:4](=S)[C:5]2[S:10][C:9](=[S:11])[N:8]([C@@H:12]3[O:24][C@H:23]([CH2:25][O:26]C(=O)C)[C@H:18]([O:19]C(=O)C)[C@H:13]3[O:14]C(=O)C)[C:6]=2[N:7]=1.C([O-])([O-])=O.[K+].[K+].CC(O)=O>CO>[NH2:1][C:2]1[N:3]=[CH:4][C:5]2[S:10][C:9](=[S:11])[N:8]([C@@H:12]3[O:24][C@H:23]([CH2:25][OH:26])[C@H:18]([OH:19])[C@H:13]3[OH:14])[C:6]=2[N:7]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 11430Potassium CarbonateHCID 178476364HCID 178476364, compound

Product 1

HCID 11623838HCID 11623838, compoundYield 67.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

5-Amino-2,3-dihydro-2-thioxo-3-(2,3,5-tri-O-acetyl-β-D-xylofuranosyl)thiazolo[4,5-d]pyrimidin-7-thione (65 mg, 0.14 mmol) is dissolved in MeOH (5 mL). To this was added K2CO3 (19 mg, 0.137 mmol), and the resultant mixture was stirred for 3 h whereupon it was quenched with HOAc (140 μL, 2.4 mmol), and the solvent was removed by rotary evaporation. The crude product is submitted to HPLC purification (MeCN—H2O) yielding 30 mg (62%) of white solid: 1H NMR (400 MHz, d6-DMSO) δ 8.50 (s, 1H), 6.90 (br s, 2H), 6.45 (d, J=5.2, 1H), 5.67 (d, J=8.0, 1H), 5.49 (d, J=8.4, 1H), 5.03 (m, 1H), 4.49 (t, J=5.2, 1H), 4.02 (m, 2H), 3.72 (m, 2H). Analysis calc'd for C10H12N4O4S2.0.4H2O: C, 37.12; H, 3.99; N, 17.32; S, 19.82. Found: C, 37.53; H, 3.80; N, 17.04; S, 19.42.

Workup

  1. customthe solvent was removed by rotary evaporation
  2. customThe crude product is submitted to HPLC purification (MeCN—H2O)

Sources & evidence

ORD record
ord-c7cae67a20284062919b642d5572feed
Source dataset
uspto-grants-2009_07
Patent number
US07560544B2

Reaction notes

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