Ammonia → 2-{[(6-Hydroxy-2-imino-2,3-dihydro-9H-purin-9-yl)oxy]methyl}propane-1,3-diol

HRID 1089286Notes

Reaction equation

HRID 1089286 reaction equation
C([O:8][CH2:9][CH:10]([CH2:26][O:27]CC1C=CC=CC=1)[CH2:11][O:12][N:13]1[CH:21]=[N:20][C:19]2[C:14]1=[N:15][C:16]([NH:23]C=O)=[N:17][C:18]=2Cl)C1C=CC=CC=1.C(O)=[O:36].N>[Pd].O>[OH:8][CH2:9][CH:10]([CH2:26][OH:27])[CH2:11][O:12][N:13]1[CH:21]=[N:20][C:19]2[C:18](=[O:36])[NH:17][C:16]([NH2:23])=[N:15][C:14]1=2

Participants

6

Reactant 3

HCID 222AmmoniaHCID 284Formic AcidHCID 22160551HCID 22160551, compound

Product 1

HCID 1354350962-{[(6-Hydroxy-2-imino-2,3-dihydro-9H-purin-9-yl)oxy]methyl}propane-1,3-diolYield 32%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 9-(3-benzyloxy-2-benzyloxymethylprop-1-oxy)-2-formamido-6-chloropurine (2.5 g, 5.2 mmol) and 80% formic acid (100 ml) was stirred at 100° C. for 1 hour, cooled and 10% palladium on charcoal (2.0 g) added. The mixture was then stirred under an atmosphere of hydrogen for 45 minutes. The catalyst was removed and the solution evaporated under reduced pressure. The residue obtained was heated in water (100 ml) until boiling commenced. Concentrated aqueous ammonia (4 ml) was added and the solution was then heated for a further 15 minutes, cooled and evaporated under reduced pressure. Recrystallisation from water (charcoal) afforded 9-(3-hydroxy-2-hydroxymethylprop-1-oxy)guanine (430 mg, 32%). IR: υmax (KBr) 3380, 3183, 1679, 1637, 1605, 1541, 1479, 1395 cm-1. 1H NMR: δH [(CD3)2SO] 1.94 (1H, m, CH), 3.53 (4H, m, 2×CH2OH), 4.26 (2H, d, J=6.3 Hz), 4.57 (2H, t, J=5.2 Hz, D2O exchangeable, 2×OH), 6.58 (2H, br.s, NH2), 7.92 (1H, s, H-8), 10.64 (1H, br.s, D2O exchangeable, H-1). Found: C, 42.08; H, 5.15; N, 27.41%. C9H13N5O4 requires: C, 42.34; H, 5.14; N, 27.44%.

Workup

  1. temperaturecooled
  2. stirringThe mixture was then stirred under an atmosphere of hydrogen for 45 minutes
  3. customThe catalyst was removed
  4. customthe solution evaporated under reduced pressure
  5. customThe residue obtained
  6. temperaturethe solution was then heated for a further 15 minutes
  7. temperaturecooled
  8. customevaporated under reduced pressure
  9. customRecrystallisation from water (charcoal)

Sources & evidence

ORD record
ord-1a136bb372c94abcae8f38c17f683300
Source dataset
uspto-grants-1990_10
Patent number
US04965270

Reaction notes

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