Methyl iodide → HCID 67846132, compound

HRID 724797Notes

Reaction equation

HRID 724797 reaction equation
[CH3:1][C@@:2]1([OH:21])[C@H:6]([O:7][CH3:8])[C@@H:5]([CH2:9][OH:10])[O:4][C@H:3]1[N:11]1[C:20]2[N:19]=[CH:18][N:17]=[C:15]([NH2:16])[C:14]=2[N:13]=[CH:12]1.[CH3:22]I>CC(C)C(N)=O>[CH3:22][NH:16][C:15]1[C:14]2[N:13]=[CH:12][N:11]([C:20]=2[N:19]=[CH:18][N:17]=1)[C@@H:3]1[O:4][C@H:5]([CH2:9][OH:10])[C@@H:6]([O:7][CH3:8])[C@@:2]1([CH3:1])[OH:21]

Participants

4

Reactant 2

HCID 6328Methyl iodideHCID 67643248HCID 67643248, compound

Product 1

HCID 67846132HCID 67846132, compound

Reagents, catalysts & solvents 1

HCID 68424IsobutyramideSolvent

Procedure

2 g of the compound obtained in Example 2 and 2 ml of methyl iodide were dissolved in dimethylacetoamide, and stirred overnight at room temperature. The reaction mixture was concentrated to dryness under reduced pressure and 10 ml of 2N sodium hydroxide solution was added thereto. The solution was refluxed for one hour with heating. After cooling to room temperature, the solution was neutralized with 2N HCl and applied on Amberlite XAD-7 column. The column was washed with water and eluted with 50% (V/V) aqueous solution of methanol. The eluate was concentrated to dryness under reduced pressure and recrystallized from ethyl acetate to give 1.8 g of N6,2',3'-O-trimethyladenosine (Compound 60).

Workup

  1. concentrationThe reaction mixture was concentrated to dryness under reduced pressure and 10 ml of 2N sodium hydroxide solution
  2. additionwas added
  3. temperatureThe solution was refluxed for one hour
  4. temperaturewith heating
  5. temperatureAfter cooling to room temperature
  6. washThe column was washed with water
  7. washeluted with 50% (V/V) aqueous solution of methanol
  8. concentrationThe eluate was concentrated to dryness under reduced pressure
  9. customrecrystallized from ethyl acetate

Sources & evidence

ORD record
ord-f1b997bcf49b49dfbd27e849b0f777bc
Source dataset
uspto-grants-1998_01
Patent number
US05705491

Reaction notes

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