HCID 22160550, compound → HCID 22160570, compound

HRID 1089285Notes

Reaction equation

HRID 1089285 reaction equation
[NH2:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[O:11][CH2:12][CH2:13][CH2:14][O:15]CC2C=CC=CC=2)=[C:4]([O:23][CH2:24][CH3:25])[N:3]=1>[Pd].C(O)=O>[NH2:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[O:11][CH2:12][CH2:13][CH2:14][OH:15])=[C:4]([O:23][CH2:24][CH3:25])[N:3]=1

Participants

4

Reactant 1

HCID 22160550HCID 22160550, compound

Product 1

HCID 22160570HCID 22160570, compoundYield 56.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 284Formic AcidSolvent

Conditions

Temperature
20 °C

Procedure

A mixture of 2-amino-9-(3-benzyloxyprop-1-oxy)-6-ethoxypurine (350 mg, 1.02 mmol), 10% palladium on charcoal (350 mg) and 80% formic acid (10 ml) was stirred at 20° C. under an atmosphere of hydrogen for 45 minutes. The catalyst was removed and the solution was evaporated under reduced pressure. The residue was dissolved in water (10 ml) and heated to boiling. Concentrated aqueous ammonia (1 ml) was then added and the solution heated for 15 minutes and then cooled and evaporated under reduced pressure. Recrystallisation of the residue from water afforded the title compound (145 mg, 56%). IR: υmax (KBr) 3376, 3326, 3205, 1649, 1611, 1581, 1509, 1454, 1402 cm-1. 1H NMR: δH [(CD3)2SO] 1.35 (3H, dd, J=6.9, 7.1 Hz, CH2CH2O), 2.50 (2H, quintet, J=6.3, 6.6 Hz, CH2), 3.56 (2H, dt, J=5.2, 6.3 Hz, CH2OH), 4.35 (2H, t, J=6.6 Hz, CH 2 ON), 4.45 (2H, quartet, J=6.9, 7.1 Hz, OCH2CH3), 4.61 (1H, t, J=5.2 Hz, D2O exchangeable, OH), 6.56 (2H, br.s, D2O exchangeable, NH2), 8.09 (1H, s, H-8). Found: C, 47.16; H, 5.92; N, 27.60%. C10H15N5O3 requires: C, 47.41; H, 5.98; N, 27.65%.

Workup

  1. customThe catalyst was removed
  2. customthe solution was evaporated under reduced pressure
  3. dissolutionThe residue was dissolved in water (10 ml)
  4. temperatureheated to boiling
  5. additionConcentrated aqueous ammonia (1 ml) was then added
  6. temperaturethe solution heated for 15 minutes
  7. temperaturecooled
  8. customevaporated under reduced pressure
  9. customRecrystallisation of the residue from water

Sources & evidence

ORD record
ord-83bd351d74b14c73ac258141d85556d7
Source dataset
uspto-grants-1990_10
Patent number
US04965270

Reaction notes

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