Acetic Acid → HCID 22819079, compound

HRID 1447005Notes

Reaction equation

HRID 1447005 reaction equation
[NH2:1][C:2]1[NH:7][C:6](=[O:8])[C:5]2[N:9]([C@@H:12]3[O:32][C@H:31]([CH2:33][O:34]CC4C=CC=CC=4)[C@@H:22]([O:23]CC4C=CC=CC=4)[C@@H:13]3[O:14]CC3C=CC=CC=3)[CH:10]=[N:11][C:4]=2[CH:3]=1.C(O)(=O)C.COC(O)C>[Pd].O>[NH2:1][C:2]1[NH:7][C:6](=[O:8])[C:5]2[N:9]([C@@H:12]3[O:32][C@H:31]([CH2:33][OH:34])[C@@H:22]([OH:23])[C@@H:13]3[OH:14])[CH:10]=[N:11][C:4]=2[CH:3]=1

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 30156371-MethoxyethanolHCID 53853974HCID 53853974, compound

Product 1

HCID 22819079HCID 22819079, compoundYield 13.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 962WaterSolvent

Procedure

A mixture of 5.9 g of 6-amino-3-(2,3,5-tri-O-benzyl-β-D-arabinofuranosyl)-3,5-dihydro-4H-imidazo-[4,5-c]pyridin-4-one, one g of 20% palladium on carbon, 5 ml of acetic acid, and 95 ml of methoxyethanol is hydrogenated at 50° C. and ca 3 atmospheres until hydrogen uptake ceases, the mixture is filtered, evaporated in vacuo, and co-evaporated with xylenes to provide a syrup which is dissolved in water and treated with 50 ml of wet IR-45 ion exchange resin. The resin is filtered, washed several times with boiling water and the combined filtrates are evaporated in vacuo to provide 2.5 g of crude product. Recrystallization from ethanol-water provides 0.42 g of 6-amino-3-β-D-arabinofuranosyl-3,5-dihydro-4H-imidazo[4,5-c]pyridin-4-one.

Workup

  1. customis hydrogenated at 50° C.
  2. filtrationca 3 atmospheres until hydrogen uptake ceases, the mixture is filtered
  3. customevaporated in vacuo
  4. customto provide a syrup which
  5. additiontreated with 50 ml of wet IR-45 ion exchange resin
  6. filtrationThe resin is filtered
  7. washwashed several times with boiling water
  8. customthe combined filtrates are evaporated in vacuo
  9. customto provide 2.5 g of crude product
  10. customRecrystallization from ethanol-water

Sources & evidence

ORD record
ord-b6e21f13abac4a85b6094c7357dac1d1
Source dataset
uspto-grants-1982_02
Patent number
US04315000

Reaction notes

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