1-Methoxyethanol → HCID 22819077, compound

HRID 1447004Notes

Reaction equation

HRID 1447004 reaction equation
[NH2:1][C:2]1[NH:7][C:6](=[O:8])[C:5]2[N:9]=[CH:10][N:11]([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)[C:4]=2[CH:3]=1.COC(O)C.[H][H]>[Pd].C(O)(=O)C>[NH2:1][C:2]1[NH:7][C:6](=[O:8])[C:5]2[N:9]=[CH:10][N:11]([C@@H:12]3[O:32][C@H:31]([CH2:33][OH:34])[C@@H:22]([OH:23])[C@@H:13]3[OH:14])[C:4]=2[CH:3]=1

Participants

6

Reactant 3

HCID 30156371-MethoxyethanolHCID 53863492HCID 53863492, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 22819077HCID 22819077, compoundYield 83.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

A mixture of 7.5 g of 6-amino-1-(2,3,5-tri-O-benzyl-β-D-arabinofuranosyl)-1,5-dihydro-4H-imidazo[4,5-c]-pyridin-4-one, 1.5 g of 20% palladium on carbon, 6.4 ml of acetic acid, and 150 ml of methoxy-ethanol is hydrogenated at 50° C. and ca 3 atmospheres until uptake of hydrogen ceases. The mixture is filtered, evaporated in vacuo, dissolved in water, and treated with 50 ml of wet IR-45 ion exchange resin. The filtrate is concentrated to dryness in vacuo and recrystallized from ethanol-water to provide 3.2 g of 6-amino-1-β-D-arabinofuranosyl-1,5-dihydro-4H-imidazo[4,5-c]pyridin-4-one.

Workup

  1. customis hydrogenated at 50° C.
  2. filtrationThe mixture is filtered
  3. customevaporated in vacuo
  4. dissolutiondissolved in water
  5. additiontreated with 50 ml of wet IR-45 ion exchange resin
  6. concentrationThe filtrate is concentrated to dryness in vacuo
  7. customrecrystallized from ethanol-water

Sources & evidence

ORD record
ord-abe2e9010ba54a3ea5b6534d52ec7338
Source dataset
uspto-grants-1982_02
Patent number
US04315000

Reaction notes

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