6-Chloropurine → HCID 18354139, compound

HRID 429013Notes

Reaction equation

HRID 429013 reaction equation
CC(C)([O-])C.[K+].[CH:7]([CH:9]([O:16][CH2:17][CH2:18][CH2:19][OH:20])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[CH2:8].Cl[C:22]1[N:30]=[CH:29][N:28]=[C:27]2[C:23]=1[NH:24][CH:25]=[N:26]2>O1CCCC1>[CH:7]([CH:9]([O:16][CH2:17][CH2:18][CH2:19][O:20][C:22]1[N:30]=[CH:29][N:28]=[C:27]2[C:23]=1[NH:24][CH:25]=[N:26]2)[C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1)=[CH2:8]

Participants

5

Reactant 3

HCID 53592776-ChloropurineHCID 18354140HCID 18354140, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 18354139HCID 18354139, compoundYield 56.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Potassium tert-butoxide (35.64 g, 0.317 mol) was added to a stirred solution of 3-(vinylbenzyloxy)-1-propanol (mixture of meta and para isomers) (30.51 g, 0.158 mol) in dry tetrahydrofuran (300 ml) under an atmosphere of nitrogen. After 15 min 6-chloropurine (24.55 g, 0.159 mol) was added, and, after stirring for 15 min at room temperature, the reaction mixture was heated at reflux overnight. The reaction mixture was allowed to cool and then the solvent was removed in vacuo. First water (600 ml) then concentrated hydrochloric acid (17 ml) were added to the residue and stirred for 15 min. The acidic mixture was neutralized with saturated sodium hydrogen carbonate solution. After stirring for 15 min the solid was removed by filtration from the neutral suspension and dried. The solid was extracted with hot tetrahydrofuran (400 ml) for 2 hr and then the undissolved material was removed by filtration whilst hot. The filtrate was concentrated in vacuo and the residue (40.5 g of a yellow solid) recrystallized from tetrahydrofuran. This gave the title compound (27.78 g, 89.6 mmol, 56%) as a yellow solid.

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureat reflux overnight
  3. temperatureto cool
  4. customthe solvent was removed in vacuo
  5. additionFirst water (600 ml) then concentrated hydrochloric acid (17 ml) were added to the residue
  6. stirringstirred for 15 min
  7. stirringAfter stirring for 15 min the solid
  8. customwas removed by filtration from the neutral suspension
  9. customdried
  10. extractionThe solid was extracted with hot tetrahydrofuran (400 ml) for 2 hr
  11. customthe undissolved material was removed by filtration whilst hot
  12. concentrationThe filtrate was concentrated in vacuo
  13. customthe residue (40.5 g of a yellow solid) recrystallized from tetrahydrofuran

Sources & evidence

ORD record
ord-2849ff86fd404885b03fee899e87c060
Source dataset
uspto-grants-2001_11
Patent number
US06316177B1

Reaction notes

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