Ethanol → 9-Hydroxy-6-phthalimidopurine

HRID 6252

Reaction equation

HRID 6252 reaction equation
C([O:8][N:9]1[CH:17]=[N:16][C:15]2[C:10]1=[N:11][CH:12]=[N:13][C:14]=2[N:18]1[C:22](=[O:23])[C:21]2=[CH:24][CH:25]=[CH:26][CH:27]=[C:20]2[C:19]1=[O:28])C1C=CC=CC=1.C(O)C>[Pd].O1CCCC1>[OH:8][N:9]1[CH:17]=[N:16][C:15]2[C:10]1=[N:11][CH:12]=[N:13][C:14]=2[N:18]1[C:22](=[O:23])[C:21]2=[CH:24][CH:25]=[CH:26][CH:27]=[C:20]2[C:19]1=[O:28]

Participants

5

Reactant 2

HCID 702EthanolHCID 145239699-Benzyloxy-6-phthalimidopurine

Product 1

HCID 145239709-Hydroxy-6-phthalimidopurineYield 83.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
25 °C

Procedure

A mixture of 9-benzyloxy-6-phthalimidopurine (11.0 g, 29.5 mmol), 10% palladium on charcoal (2.2 g), ethanol (300 ml) and tetrahydrofuran (500 ml) was stirred at 25° C. for 1 hour under an atmosphere of hydrogen. The suspension was then filtered and the catalyst washed with ethanol. The filtrate was evaporated under reduced pressure and the resulting solid triturated with ether. The solid was collected and then dried to afford the title compound (6.93 g; 83%). IR: νmax (KBr). 2607, 1794, 1735, 1603, 1582, 1467, 1401 cm-1 ; 1H NMR δH [(CD3)2SO] 8.15(4H, s, Ar), 8.95(1H, s, H-2), 9.15(1H, s, H-8), 12.80(1H, br.s, D2O exchangeable, OH). Found: C, 55.34; H, 2.58; N, 24.56%. C13H7N5O3 requires: C, 55.51; H, 2.51; N, 24.91%.

Workup

  1. filtrationThe suspension was then filtered
  2. washthe catalyst washed with ethanol
  3. customThe filtrate was evaporated under reduced pressure
  4. customthe resulting solid triturated with ether
  5. customThe solid was collected
  6. customdried

Sources & evidence

ORD record
ord-bcb1f28502a14261b19c5dc4802361c3
Source dataset
uspto-grants-1993_09
Patent number
US05247085

Linked notes

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