Triethylamine → HCID 9860535, compound

HRID 1655935Notes

Reaction equation

HRID 1655935 reaction equation
Cl[C:2]1[N:10]=[C:9]([NH:11]C=O)[N:8]=[C:7]2[C:3]=1[N:4]=[CH:5][N:6]2[O:14][CH2:15][CH2:16][CH2:17][O:18][CH2:19][O:20][CH:21]([CH3:23])[CH3:22].C(N(CC)CC)C>[Pd].CO>[NH2:11][C:9]1[N:8]=[C:7]2[C:3]([N:4]=[CH:5][N:6]2[O:14][CH2:15][CH2:16][CH2:17][O:18][CH2:19][O:20][CH:21]([CH3:23])[CH3:22])=[CH:2][N:10]=1

Participants

5

Reactant 2

HCID 8471TriethylamineHCID 19789735HCID 19789735, compound

Product 1

HCID 9860535HCID 9860535, compoundYield 41.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Conditions

Temperature
20 °C

Procedure

A mixture of 6-chloro-2-formamido-9-[3-(isopropoxymethoxy)propoxy]purine (1.86 g, 5.40 mmol), 10% palladium on charcoal (190 mg), triethylamine (3.8 ml, 27 mmol) and methanol (30 ml) was stirred under an atmosphere of hydrogen at 20° C. for 4 hr. The suspension was filtered, the catalyst washed with chloroform and the combined filtrates evaporated under reduced pressure. The residue was dissolved in dichloromethane (50 ml), washed with saturated brine-water (2:1), dried (magnesium sulphate) and evaporated. The residue was dissolved in 0.5M sodium methoxide in methanol (21.6 ml) and heated at reflux for 1 hr. The solution was taken to neutrality using AMBERLITE IR 120(H) and evaporated. The residue was purified by column chromatography on silica gel eluting with chloroform-methanol (20:1) affording the title compound (630 mg, 41%) after recrystallisation from acetone-hexane; νmax (KBr) 3333, 3192, 1661, 1623, 1577, 1516, 1433 cm-1 ; δH [(CD3 )2SO] 1.09 (6H, d, J 6.05 Hz, 2×CH3), 1.95 (2H, quintet, J 6.6 and 6.3 Hz, CH2CH2CH2), 3.63 (2H, t, J=6.3 Hz, CH2OC), 3.77 (1H, septet, J=6.0 Hz, CH), 4.39 (2H, J=6.6 Hz, CH2ON), 4.64 (2H, s, OCH2O), 6.69 (2H, br.s, D2O exchangeable, NH2), 8.31 (1H, s, H-8), 8.59 (1H, s, H-6). Found: C, 51.21; H, 6.84; N, 24.82%; C12H19N5O3 requires: C, 51.22; H, 6.82; N, 24.89%.

Workup

  1. filtrationThe suspension was filtered
  2. washthe catalyst washed with chloroform
  3. customthe combined filtrates evaporated under reduced pressure
  4. dissolutionThe residue was dissolved in dichloromethane (50 ml)
  5. washwashed with saturated brine-water (2:1)
  6. dry with materialdried (magnesium sulphate)
  7. customevaporated
  8. dissolutionThe residue was dissolved in 0.5M sodium methoxide in methanol (21.6 ml)
  9. temperatureheated
  10. temperatureat reflux for 1 hr
  11. customevaporated
  12. customThe residue was purified by column chromatography on silica gel eluting with chloroform-methanol (20:1)

Sources & evidence

ORD record
ord-c28184a4e43b4a118e2e87d671ffa45d
Source dataset
uspto-grants-1993_10
Patent number
US05252575

Reaction notes

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