1-Methoxyethanol → HCID 54265562, compound

HRID 1447007Notes

Reaction equation

HRID 1447007 reaction equation
[NH2:1][C:2]1[C:7]2[N:8]([C@@H:11]3[O:31][C@H:30]([CH2:32][O:33]CC4C=CC=CC=4)[C@@H:21]([O:22]CC4C=CC=CC=4)[C@@H:12]3[O:13]CC3C=CC=CC=3)[CH:9]=[N:10][C:6]=2[CH:5]=[C:4]([NH2:41])[N:3]=1.COC(O)C.[H][H]>[Pd].C(O)(=O)C>[C@@H:11]1([N:8]2[C:7]3[C:2]([NH2:1])=[N:3][C:4]([NH2:41])=[CH:5][C:6]=3[N:10]=[CH:9]2)[O:31][C@H:30]([CH2:32][OH:33])[C@@H:21]([OH:22])[C@@H:12]1[OH:13]

Participants

6

Reactant 3

HCID 30156371-MethoxyethanolHCID 53719475HCID 53719475, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 54265562HCID 54265562, compoundYield 78.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

A mixture of 5.0 g of 4,6-diamino-3-(2,3,5-tri-O-benzyl-β-D-arabinofuranosyl)-3H-imidazo[4,5-c]pyridine, 1.5 g of 20% palladium on carbon, 1.6 ml of acetic acid and 150 ml of methoxyethanol 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 and recrystallized from ethanol-water to provide 2.0 g of 3-β-D-arabinofuranosyl-4,6-diamino-3H-imidazo-[4,5-c]pyridine.

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
  7. customrecrystallized from ethanol-water

Sources & evidence

ORD record
ord-62f237ac6bc543609dca096b2ebbf9e0
Source dataset
uspto-grants-1982_02
Patent number
US04315000

Reaction notes

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