Adenine → Ro 24-5098

HRID 893610Notes

Reaction equation

HRID 893610 reaction equation
[N:1]1[C:9]([NH2:10])=[C:8]2[C:4]([N:5]=[CH:6][NH:7]2)=[N:3][CH:2]=1.C1OCCOCCOCCOCCOCCOC1.CC1C=CC(S(O[C@@H:40]2[CH2:44][O:43][C@@H:42]([CH2:45][OH:46])[CH2:41]2)(=O)=O)=CC=1>CN(C=O)C>[NH2:10][C:9]1[N:1]=[CH:2][N:3]=[C:4]2[C:8]=1[N:7]=[CH:6][N:5]2[C@H:40]1[CH2:44][O:43][C@@H:42]([CH2:45][OH:46])[CH2:41]1

Participants

5

Reactant 3

HCID 190AdenineHCID 2855718-Crown-6HCID 14606665HCID 14606665, compound

Product 1

HCID 124453Ro 24-5098Yield 29%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a flame-dried argon blanketed round bottom flask equipped with a magnetic stir bar and condenser was added adenine (50 mg, 0.37 mmole) K2CO3 (100 mg, 0.73 mmole), 18-crown-6 (97 mg, 0.37 mmole) and DMF (10 mL). This mixture was allowed to stir at room temperature for 30 minutes under a stream of argon. A solution of (2R-trans)-tetrahydro-4-[[(4-methylphenyl)sulfonyl]oxy]-2-furanmethanol, Compound IV(c), (100 mg, 0.37 mmole) in 2 mL DMF was then added dropwise to the stirring mixture. The resultant mixture was warmed to 80° C., and stirred at that temperature overnight. After removal of the solvent in vacuo, the solid residue was purified by flash chromatorgraphy using a 10% MeOH/90% CH2Cl2 solution as eluant. This isolated material was further purified by reverse-phase HPLC using a gradient elution system of CH3CN/H2O to yield 25 mg (29%) of Compound I as a white solid. An analytical sample was crystallized from methanol: mp 183°-185°, [α]D +47.91 (c 0.67, MeOH).

Workup

  1. customTo a flame-dried argon blanketed round bottom flask equipped with a magnetic stir bar and condenser
  2. stirringstirred at that temperature overnight
  3. customAfter removal of the solvent in vacuo
  4. customthe solid residue was purified by flash chromatorgraphy
  5. customThis isolated material was further purified by reverse-phase

Sources & evidence

ORD record
ord-966c8465a618423ebfe0cbb64ddc7423
Source dataset
uspto-grants-1992_06
Patent number
US05126347

Reaction notes

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