1-Methoxyethanol → HCID 135409288, compound

HRID 223168Notes

Reaction equation

HRID 223168 reaction equation
[NH2:1][C:2]1[N:3]=[C:4]([O:41]CC=C)[C:5]2[CH:10]=[CH:9][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)[C:6]=2[N:7]=1.COC(O)C.[H][H]>[Pd].C(O)(=O)C>[NH2:1][C:2]1[NH:3][C:4](=[O:41])[C:5]2[CH:10]=[CH:9][N:8]([C@@H:11]3[O:31][C@H:30]([CH2:32][OH:33])[C@@H:21]([OH:22])[C@@H:12]3[OH:13])[C:6]=2[N:7]=1

Participants

6

Reactant 3

HCID 30156371-MethoxyethanolHCID 22821688HCID 22821688, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 135409288HCID 135409288, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

A mixture of 8.0 g of 2-amino-4-allyloxy-7-(2,3,5-tri-O-benzyl-β-D-arabinofuranosyl)-7H-pyrrolo[2,3-d]pyrimidine, 1.5 g of 20% palladium on charcoal, 6.7 ml of acetic acid, and 150 ml of methoxy ethanol is hydrogenated at 50° C. and approximately 3 atmospheres until the uptake of hydrogen ceases. The mixture is filtered, evaporated in vacuo, dissolved in water, and treated with 60 ml of wet IR-45 ion exchange resin. The filtrate is concentrated to dryness in vacuo and the residue is recrystallized from water to provide pure 2-amino-7-β-D-arabinofuranosyl-3,7-dihydro-4H-pyrrolo[2,3-d]pyrimidin-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 60 ml of wet IR-45 ion exchange resin
  6. concentrationThe filtrate is concentrated to dryness in vacuo
  7. customthe residue is recrystallized from water

Sources & evidence

ORD record
ord-7246a0cd86f5402d9ca0f0b7431c2cd6
Source dataset
uspto-grants-1982_10
Patent number
US04352795

Reaction notes

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