Formic Acid → 9-(3-Hydroxypropoxy)guanine

HRID 1089283Notes

Reaction equation

HRID 1089283 reaction equation
C([O:8][CH2:9][CH2:10][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:27]>[Pd]>[OH:8][CH2:9][CH2:10][CH2:11][O:12][N:13]1[CH:21]=[N:20][C:19]2[C:18](=[O:27])[NH:17][C:16]([NH2:23])=[N:15][C:14]1=2

Participants

4

Reactant 2

HCID 284Formic AcidHCID 13989894HCID 13989894, compound

Product 1

HCID 1354093719-(3-Hydroxypropoxy)guanineYield 33%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

9-(3-Benzyloxyprop-1-oxy)-6-chloro-2-formamidopurine (3.40 g, 9.41 mmol) in 80% formic acid (100 ml) was heated at 100° C. for 1 hour. The reaction mixture was then cooled and stirred with 10% palladium on charcoal (2.0 g) under an atmosphere of hydrogen at 20° C. for 45 minutes. After removal of the catalyst, the solution was evaporated and the residue was treated with water (50 ml) and concentrated aqueous ammonia (4 ml) at 100° C. for 15 minutes. The solution was then cooled and evaporated under reduced pressure. Recrystallisation of the residue from water afforded 9-(3-hydroxyprop-1-oxy)guanine (800 mg, 33%). 1H NMR: δH [(CD3)2SO] 1.80 (2H, quintet, J=6.3, 6.6 Hz, CH2CH2CH2), 3.55 (2H, quartet, J=5.50, 5.8 Hz, CH2OH), 4.32 (2H, t, J=6.6 Hz, CH2ON), 4.57 (1H, t, J=5.5 Hz, D2O exchangeable, OH), 6.57 (2H, br.s, D2O exchangeable, NH2), 7.91 (1H, s, H-8), 10.63 (1H, br.s, D2O exchangeable, H-1).

Workup

  1. temperatureThe reaction mixture was then cooled
  2. customAfter removal of the catalyst
  3. customthe solution was evaporated
  4. additionthe residue was treated with water (50 ml) and concentrated aqueous ammonia (4 ml) at 100° C. for 15 minutes
  5. temperatureThe solution was then cooled
  6. customevaporated under reduced pressure
  7. customRecrystallisation of the residue from water

Sources & evidence

ORD record
ord-da171665052642b1a9a2371efdb91894
Source dataset
uspto-grants-1990_10
Patent number
US04965270

Reaction notes

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