1-Propanol → HCID 22854550, compound

HRID 1901522Notes

Reaction equation

HRID 1901522 reaction equation
Cl[C:2]1[N:3]=[C:4]([NH:20][N:21]2[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]2)[C:5]2[N:6]=[CH:7][N:8]([C:18]=2[N:19]=1)[C@@H:9]1[O:17][C@H:14]([CH2:15][OH:16])[C@@H:12]([OH:13])[C@H:10]1[OH:11].[OH-].[Na+].[CH2:29]([OH:32])[CH2:30][CH3:31]>>[N:21]1([NH:20][C:4]2[C:5]3[N:6]=[CH:7][N:8]([C:18]=3[N:19]=[C:2]([O:32][CH2:29][CH2:30][CH3:31])[N:3]=2)[C@@H:9]2[O:17][C@H:14]([CH2:15][OH:16])[C@@H:12]([OH:13])[C@H:10]2[OH:11])[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]1

Participants

4

Reactant 3

HCID 10311-PropanolHCID 14798Sodium HydroxideHCID 10022940HCID 10022940, compound

Product 1

HCID 22854550HCID 22854550, compoundYield 37%

Procedure

2-Chloro-N-(1-piperidinyl)adenosine (0.50 g, 1.3 mmol) (Example 5) was dissolved in a solution of sodium hydroxide (0.51 g, 1.3 mmol) in 1-propanol (15 ml), and the solution was heated at reflux for 4.5 hours, after which time TLC investigation showed that the starting material had been consumed. The reaction mixture was evaporated and the resultant residue was dissolved in water. The solution was neutralized with 4N aqueous hydrochloric acid and extracted with dichloromethane (3×50 ml). The combined extracts were dried (MgSO4) and evaporated to an oil which was triturated with diethyl ether to afford a fawn foam. This foam was purified by column chromatography on silica gel (2×20 cm); elution with a mixture of dichloromethane/ethanol 25% aqueous ammonia solution (60/10/1) provided the title compound (0.20 g, 37%) as a semi-solid foam; 1H NMR (400 MHz, Me2SO-d6) δ 3.54, 3.65 (2H, ABX, H-5'a and H-5'b), 3.92 (1H, q, H-4'), 4.15 (1H, q, H-3'), 4.60 (1H, q, H-2'), 5.80 (1H, d, H-1'), 8.16 (1H, s, H-8).

Workup

  1. temperaturethe solution was heated
  2. temperatureat reflux for 4.5 hours
  3. customhad been consumed
  4. customThe reaction mixture was evaporated
  5. dissolutionthe resultant residue was dissolved in water
  6. extractionextracted with dichloromethane (3×50 ml)
  7. dry with materialThe combined extracts were dried (MgSO4)
  8. customevaporated to an oil which
  9. customwas triturated with diethyl ether
  10. customto afford a fawn foam
  11. customThis foam was purified by column chromatography on silica gel (2×20 cm)
  12. washelution
  13. additionwith a mixture of dichloromethane/ethanol 25% aqueous ammonia solution (60/10/1)

Sources & evidence

ORD record
ord-c0cc390e36ad4760a6edf2797e8cb157
Source dataset
uspto-grants-1996_11
Patent number
US05578582

Reaction notes

Loading…