Acetic Acid → 7-beta-D-Arabinofuranosyl-7H-pyrrolo(2,3-d)pyrimidin-4-amine

HRID 223158Notes

Reaction equation

HRID 223158 reaction equation
C([O:8][C@H:9]1[C@H:13]([O:14]CC2C=CC=CC=2)[C@@H:12]([CH2:22][O:23]CC2C=CC=CC=2)[O:11][C@H:10]1[N:31]1[C:35]2[N:36]=[CH:37][N:38]=[C:39]([NH2:40])[C:34]=2[CH:33]=[CH:32]1)C1C=CC=CC=1.C(O)(=O)C.COC(O)C.[H][H]>[Pd].O>[C@@H:10]1([N:31]2[C:35]3[N:36]=[CH:37][N:38]=[C:39]([NH2:40])[C:34]=3[CH:33]=[CH:32]2)[O:11][C@H:12]([CH2:22][OH:23])[C@@H:13]([OH:14])[C@@H:9]1[OH:8]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 30156371-MethoxyethanolHCID 130762157-(2,3,5-tri-O-benzyl-beta-D-arabinofuranosyl)-7H-pyrrolo[2,3-d]pyrimidin-4-amineHCID 178418361HCID 178418361, compound

Product 1

HCID 30079187-beta-D-Arabinofuranosyl-7H-pyrrolo(2,3-d)pyrimidin-4-amineYield 80%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 962WaterSolvent

Procedure

A mixture of 2.5 g of 7-(2,3,5-tri-O-benzyl-β-D-arabinofuranosyl)-7H-pyrrolo[2,3-d]pyrimidin-4-amine, 5 ml of acetic acid, 500 mg of 20% of palladium on charcoal, and 95 ml of methoxyethanol is hydrogenated at 50°-55° C. and approximately 3 atmospheres until uptake of hydrogen ceases. The mixture is filtered, evaporated in vacuo, and coevaporated with xylenes to provide a red syrup which is dissolved in water and treated with Amberlite ion exchange resin (20 ml of wet IR-45). The resin is filtered and washed several times with boiling water. The combined filtrates are evaporated in vacuo to provide 992 mg of crude 7-βD-arabinofuranosyl-7H-pyrrolo[2,3-d]pyrimidin-4-amine. Recrystallization of this material from water provides 800 mg of product, m.p. 117°-120° C. (after drying at 100° C. for one hour); [α]D25 =+16.2 (1.02% in H2O).

Workup

  1. customis hydrogenated at 50°-55° C.
  2. filtrationThe mixture is filtered
  3. customevaporated in vacuo
  4. customto provide a red syrup which
  5. additiontreated with Amberlite ion exchange resin (20 ml of wet IR-45)
  6. filtrationThe resin is filtered
  7. washwashed several times with boiling water
  8. customThe combined filtrates are evaporated in vacuo

Sources & evidence

ORD record
ord-914e99182e304a11983b762119ca3c19
Source dataset
uspto-grants-1982_10
Patent number
US04352795

Reaction notes

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