Dimethylformamide diethylacetal → HCID 136351321, compound

HRID 481738Notes

Reaction equation

HRID 481738 reaction equation
[C@@H:1]1([N:9]2[C:13]3[N:14]=[C:15]([NH2:19])[NH:16][C:17](=[O:18])[C:12]=3[N:11]=[N:10]2)[O:6][C@H:5]([CH2:7][OH:8])[C@@H:3]([OH:4])[CH2:2]1.C(O[CH:23](OCC)[N:24]([CH3:26])[CH3:25])C>CN(C=O)C>[C@@H:1]1([N:9]2[C:13]3[N:14]=[C:15]([N:19]=[CH:23][N:24]([CH3:26])[CH3:25])[NH:16][C:17](=[O:18])[C:12]=3[N:11]=[N:10]2)[O:6][C@H:5]([CH2:7][OH:8])[C@@H:3]([OH:4])[CH2:2]1

Participants

4

Reactant 2

HCID 70913Dimethylformamide diethylacetalHCID 136108872HCID 136108872, compound

Product 1

HCID 136351321HCID 136351321, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3-(2-Deoxy-β-D-erythropentofuranosyl)-5-amino-3H-1,2,3-triazolo[4,5-d]pyrimidin-7-(6H)-one (8-aza-2'-deoxyguanosine (1)) (290 mg; 1.06 mmol) was dissolved in abs. DMF (7 ml), and N,N-dimethylformamide diethyl acetal (5 ml) was added. After the mixture had been stirred at room temperature for 24 hours, it was subjected to rotary evaporation in vacuo, and the residue was coevaporated with toluene. The residue was purified by means of chromatography on silica gel (column: 20×4 cm, 0.5 bar, CH2 Cl2 /MeOH 8:2). Compound (2) (320 mg, 92%) was obtained as a colorless foam which crystallized from MeOH. M.p. 236° C. TLC (CH2Cl2 /MeOH 8:2): Rf 0.7. UV (MeOH): 301 (26500), 244(15500).

Workup

  1. customit was subjected to rotary evaporation in vacuo
  2. customThe residue was purified by means of chromatography on silica gel (column: 20×4 cm, 0.5 bar, CH2 Cl2 /MeOH 8:2)

Sources & evidence

ORD record
ord-cfce060112bd4b8f8bf854570fca5d69
Source dataset
uspto-grants-1998_08
Patent number
US05789562

Reaction notes

Loading…