HCID 178476336, compound → 9-[(2R,5S)-5-(hydroxymethyl)-2,5-dihydrofuran-2-yl]-3H-purin-6-one

HRID 2354002Notes

Reaction equation

HRID 2354002 reaction equation
C([O:4][CH2:5][C@H:6]1[O:10][C@@H:9]([N:11]2[C:20]3[N:19]=[CH:18][N:17]=[C:15]([OH:16])[C:14]=3[N:13]=[CH:12]2)[CH:8]=[CH:7]1)(=O)C>CN>[C@@H:9]1([N:11]2[C:20]3[N:19]=[CH:18][N:17]=[C:15]([OH:16])[C:14]=3[N:13]=[CH:12]2)[O:10][C@H:6]([CH2:5][OH:4])[CH:7]=[CH:8]1

Participants

3

Reactant 1

HCID 178476336HCID 178476336, compound

Product 1

HCID 1785209639-[(2R,5S)-5-(hydroxymethyl)-2,5-dihydrofuran-2-yl]-3H-purin-6-oneYield 73.7%

Reagents, catalysts & solvents 1

HCID 6329MethylamineSolvent

Conditions

Temperature
30 °C

Procedure

5′-O-Acetyl-2′,3′-dideoxy-2′,3′-didehydroinosine (100 gm) is added to 25% monomethyl amine (360 ml) at 25-35° C. and stirred for 4-5 hours at 25-35° C. The mass is filtered on a celite bed, washed with methanol (50 ml) and the solvent is distilled off completely under reduced pressure at below 70° C. Methanol (25 ml) is added to the filtrate, the solvent is distilled off completely, and methanol (25 ml) is again added and co-distilled. To the mass, acetone (25 ml) is added, co-distilled, again co-distilled with 25 ml of acetone at below 70° C. and acetone (400 ml) is added. The contents are cooled to 25-35° C., stirred for 2 hours to 2 hours 30 minutes at 25-35° C. Then the reaction mass is cooled to 0-10° C. and stirred for 1 hour to 1 hour 30 minutes. material is filtered, washed with acetone (80 ml) and dried at 55-65° C. to give 62.5 gm of 2′,3′-dideoxy-2′,3′-didehydroinosine (HPLC Purity: 98.14%).

Workup

  1. filtrationThe mass is filtered on a celite bed
  2. washwashed with methanol (50 ml)
  3. distillationthe solvent is distilled off completely under reduced pressure at below 70° C
  4. additionMethanol (25 ml) is added to the filtrate
  5. distillationthe solvent is distilled off completely
  6. additionmethanol (25 ml) is again added
  7. additionTo the mass, acetone (25 ml) is added
  8. customagain co-distilled with 25 ml of acetone at below 70° C.
  9. additionacetone (400 ml) is added
  10. temperatureThe contents are cooled to 25-35° C.
  11. stirringstirred for 2 hours to 2 hours 30 minutes at 25-35° C
  12. temperatureThen the reaction mass is cooled to 0-10° C.
  13. stirringstirred for 1 hour to 1 hour 30 minutes
  14. filtrationmaterial is filtered
  15. washwashed with acetone (80 ml)
  16. customdried at 55-65° C.

Sources & evidence

ORD record
ord-2b07fc0f1cce4939a9576ae889ef6bf9
Source dataset
uspto-grants-2010_07
Patent number
US07750153B2

Reaction notes

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