Cesium carbonate → HCID 15667234, compound

HRID 1463782Notes

Reaction equation

HRID 1463782 reaction equation
[CH:1]([O:4][P:5]([CH2:11][O:12][C@H:13]([CH3:20])[CH2:14]OS(C)(=O)=O)([O:7][CH:8]([CH3:10])[CH3:9])=[O:6])([CH3:3])[CH3:2].[NH2:21][C:22]1[N:30]=[C:29]2[C:25]([NH:26][CH:27]=[N:28]2)=[C:24]([Cl:31])[N:23]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>C(#N)C>[NH2:21][C:22]1[N:30]=[C:29]2[C:25]([N:26]=[CH:27][N:28]2[CH2:14][C@H:13]([O:12][CH2:11][P:5]([O:4][CH:1]([CH3:2])[CH3:3])([O:7][CH:8]([CH3:9])[CH3:10])=[O:6])[CH3:20])=[C:24]([Cl:31])[N:23]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 53603492-Amino-6-chloropurineHCID 15667231HCID 15667231, compound

Product 1

HCID 15667234HCID 15667234, compoundYield 35%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

(R)-2-O-[(Diisopropylphosphono)methyl]-1-O-methanesulfonyl-1,2-propanediol (2.0 g, 6.02 mmol) was mixed with 2-amino-6-chloropurine (1 23 g, 7.22 mmol) and cesium carbonate (3.92 g, 12.0 mmol) in 40 mL of acetonitrile. The mixture was gently refluxed under nitrogen atmosphere for 24 hours, then allowed to cool to room temperature, and filtered. The solvent was removed under reduced pressure The residue was purified by flash chromatography on silica gel twice (first time, methylene chloride:acetone=3:1 to 0:1; second time, methylene chloride:methanol=15:1 to 10:1). The title compound (0.85 g, 35% yield) was isolated as a glassy material which was crystallized from ethyl acetate-diethyl ether: mp 133°-135° C.

Workup

  1. temperatureThe mixture was gently refluxed under nitrogen atmosphere for 24 hours
  2. filtrationfiltered
  3. customThe solvent was removed under reduced pressure The residue
  4. customwas purified by flash chromatography on silica gel twice (first time, methylene chloride:acetone=3:1 to 0:1; second time, methylene chloride:methanol=15:1 to 10:1)

Sources & evidence

ORD record
ord-19ddb767011d4afdb4a1fd9a41896b53
Source dataset
uspto-grants-1994_04
Patent number
US05302585

Reaction notes

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