8-(4-Hydroxy-bicyclo[2.2.2]oct-1-yl)-6-(1-hydroxymethyl-propylamino)-3-propyl-3,7-dihydro-purin-2-one → 8-ethyl-2-(4-hydroxy-1-bicyclo[2.2.2]octanyl)-4-propyl-7,8-dihydro-1H-imidazo[2,1-f]purin-5-one

HRID 395278Notes

Reaction equation

HRID 395278 reaction equation
[OH:1][C:2]12[CH2:9][CH2:8][C:5]([C:10]3[NH:18][C:17]4[C:16]([NH:19][CH:20]([CH2:23]O)[CH2:21][CH3:22])=[N:15][C:14](=[O:25])[N:13]([CH2:26][CH2:27][CH3:28])[C:12]=4[N:11]=3)([CH2:6][CH2:7]1)[CH2:4][CH2:3]2>O=S(Cl)Cl>[CH2:21]([CH:20]1[N:19]=[C:16]2[N:15]([C:14](=[O:25])[N:13]([CH2:26][CH2:27][CH3:28])[C:12]3[N:11]=[C:10]([C:5]45[CH2:4][CH2:3][C:2]([OH:1])([CH2:9][CH2:8]4)[CH2:7][CH2:6]5)[NH:18][C:17]=32)[CH2:23]1)[CH3:22]

Participants

3

Reactant 1

HCID 691480518-(4-Hydroxy-bicyclo[2.2.2]oct-1-yl)-6-(1-hydroxymethyl-propylamino)-3-propyl-3,7-dihydro-purin-2-one

Product 1

HCID 1784565778-ethyl-2-(4-hydroxy-1-bicyclo[2.2.2]octanyl)-4-propyl-7,8-dihydro-1H-imidazo[2,1-f]purin-5-oneYield 47.7%

Reagents, catalysts & solvents 1

HCID 24386Thionyl ChlorideSolvent

Procedure

8-(4-Hydroxy-bicyclo[2.2.2]oct-1-yl)-6-(1-hydroxymethyl-propylamino)-3-propyl-3,7-dihydro-purin-2-one (110 mg) was dissolved in 3 mL of SOCl2 and stirred under reflux for 20 min. It was then cooled to rt and concentrated. The residue was quenched with saturated aq NaHCO3 and extracted with CHCl3. The combined organic layers were dried (Na2SO4) and concentrated under reduced pressure. Purification by preparative HPLC afforded 50 mg of the titled compound as the TFA salt.

Workup

  1. temperatureunder reflux for 20 min
  2. concentrationconcentrated
  3. customThe residue was quenched with saturated aq NaHCO3
  4. extractionextracted with CHCl3
  5. dry with materialThe combined organic layers were dried (Na2SO4)
  6. concentrationconcentrated under reduced pressure
  7. customPurification by preparative HPLC

Sources & evidence

ORD record
ord-e163617c7ed54cf9bc2b383b2e0dbb9b
Source dataset
uspto-grants-2003_08
Patent number
US06605601B2

Reaction notes

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