Potassium Carbonate → HCID 54509916, compound

HRID 1883552Notes

Reaction equation

HRID 1883552 reaction equation
[Cl:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[C@@H:11]2[O:23][C@H:22]([CH2:24][O:25]C(=O)C)[C@@H:17]([O:18]C(=O)C)[C@H:12]2[O:13]C(=O)C)=[C:4](Cl)[N:3]=1.C([O-])([O-])=O.[K+].[K+].[CH2:36]([CH:38]([NH2:41])[CH2:39][CH3:40])[CH3:37]>C(O)(C)C>[Cl:1][C:2]1[N:3]=[C:4]([NH:41][CH:38]([CH2:39][CH3:40])[CH2:36][CH3:37])[C:5]2[N:6]=[CH:7][N:8]([C:9]=2[N:10]=1)[C@@H:11]1[O:23][C@H:22]([CH2:24][OH:25])[C@@H:17]([OH:18])[C@H:12]1[OH:13]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 120193-PentanamineHCID 102530272,6-Dichloro-9-(2,3,5-tri-O-acetyl-beta-D-ribofuranosyl)purine

Product 1

HCID 54509916HCID 54509916, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
20 °C

Procedure

A mixture of 2,6-dichloro-9-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)-9H-purine ** (10.1 g, 22.6 mM), iso-propanol (300 ml), K2CO3 (5 g) and 1-ethylpropylamine (2.17 g, 24.84 mM) was stirred at 20° C. for 24 hrs. The reaction mixture was heated at 54° C. for 73 hrs. Solvent was removed in vacuo, water (50 ml) was added, extracted with ethyl acetate (3×80 ml), the combined extracts were dried (MgSO4) affording the title compound as a creamy light brown foam (9.44 g). LC/MS system A Rt=2.66 min, m/z=372 MH+.

Workup

  1. temperatureThe reaction mixture was heated at 54° C. for 73 hrs
  2. customSolvent was removed in vacuo, water (50 ml)
  3. additionwas added
  4. extractionextracted with ethyl acetate (3×80 ml)
  5. dry with materialthe combined extracts were dried (MgSO4)

Sources & evidence

ORD record
ord-6c452e7453354f22afc8a8e6afe8e7cc
Source dataset
uspto-grants-2004_07
Patent number
US06762170B1

Reaction notes

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