Ammonium formate → HCID 14814190, compound

HRID 1089288Notes

Reaction equation

HRID 1089288 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][CH:13]([OH:16])[CH2:14][OH:15])=[C:4](Cl)[N:3]=1.C([O-])=O.[NH4+]>CO.[Pd]>[NH2:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[O:11][CH2:12][CH:13]([OH:16])[CH2:14][OH:15])=[CH:4][N:3]=1

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 14814187HCID 14814187, compound

Product 1

HCID 14814190HCID 14814190, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 2-amino-6-chloro-9-(2,3-dihydroxyprop-1-oxy)purine (150 mg, 0.58 mmol), ammonium formate (146 mg, 2.32 mmol) and 10% palladium-on-charcoal (15 mg) in methanol (5 ml) was stirred under reflux for 4 hours. The reaction was evaporated under reduced pressure and the residue was dissolved in water and passed through a SEP-PAK C18 cartridge for decolourisation. After elution with water, the water was evaporated under reduced pressure and the residue recrystallised from ethanol affording the title compound (58 mg, 45%), m.p. 183°-185° C. UV: λmax (H2O) 221 (ε25,600), 305 (ε7,000) nm; IR: υmax (KBr) 3670, 3420, 3310, 3200, 1650, 1620, 1570, 1520, 1480, 1425 cm-1 ; 1H NMR: δH (CD3)2SO] 3.41 (2H, m, CH2OH), 3.76 (1H, m, CHOH), 4.18 (1H, dd, J=7.6, 10.7 Hz, CH2ON), 4.39 (1H, dd, J=3.2, 10.7 Hz, CH2ON), 4.72 (1H, t, J=5.6 Hz, OH), 5.15 (1H, d, J=5.2 Hz, OH), 6.72 (2H, br.s, NH2), 8.27 (1H, s, H-8), 8.59 (1H, s, H-6). Found: C, 42.17; H, 4.91; N, 31.07%, M+ 225.0865. C8H11N5O3 requires C, 42.67; H, 4.92; N, 31.10%, M+ 225.0862.

Workup

  1. temperatureunder reflux for 4 hours
  2. customThe reaction was evaporated under reduced pressure
  3. dissolutionthe residue was dissolved in water
  4. washAfter elution with water
  5. customthe water was evaporated under reduced pressure
  6. customthe residue recrystallised from ethanol affording the title compound (58 mg, 45%), m.p. 183°-185° C

Sources & evidence

ORD record
ord-e0a12decfc6940f08f902e84a1e7fc14
Source dataset
uspto-grants-1990_10
Patent number
US04965270

Reaction notes

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