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1-Butanol → 6-[N-Cyclopentyl-N-(2,5-dimethylbenzyl)-amino]-9-[(2-hydroxyethoxy)-methyl]-purine hydrochloride

HRID 1721841
Notes
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Reaction equation

HRID 1721841 reaction equation
C([O:9][CH2:10][CH2:11][O:12][CH2:13][N:14]1[CH:22]=[N:21][C:20]2[C:15]1=[N:16][CH:17]=[N:18][C:19]=2[Cl:23])(=O)C1C=CC=CC=1.[CH:24]1([NH:29][CH2:30][C:31]2[CH:36]=[C:35]([CH3:37])[CH:34]=[CH:33][C:32]=2[CH3:38])[CH2:28][CH2:27][CH2:26][CH2:25]1.C(O)CCC.Cl>C(OCC)(=O)C>[ClH:23].[CH:24]1([N:29]([C:19]2[N:18]=[CH:17][N:16]=[C:15]3[C:20]=2[N:21]=[CH:22][N:14]3[CH2:13][O:12][CH2:11][CH2:10][OH:9])[CH2:30][C:31]2[CH:36]=[C:35]([CH3:37])[CH:34]=[CH:33][C:32]=2[CH3:38])[CH2:28][CH2:27][CH2:26][CH2:25]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 2631-ButanolHCID 313Hydrochloric AcidHCID 129267736-Chloro-9-(2-benzoyloxyethoxymethyl)purineHCID 19864492N-[(2,5-Dimethylphenyl)methyl]cyclopentanamine

Product 1

HCID 200299776-[N-Cyclopentyl-N-(2,5-dimethylbenzyl)-amino]-9-[(2-hydroxyethoxy)-methyl]-purine hydrochlorideYield 75%

Reagents, catalysts & solvents

1
HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 9.0 g. (27 mmole) 9-[(2-benzoyloxyethoxy)-methyl]-6-chloropurine, 16.5 g. (81 mmole) N-cyclopentyl-(2,5-dimethylbenzyl)-amine and 130 ml. butanol is heated under reflux for 16 hours. The reaction mixture is evaporated, the residue is taken up in dichloromethane, washed with dilute acetic acid and subsequently with water, dried over anhydrous sodium sulphate, evaporated, mixed with a solution of 3.3 g. sodium in 200 ml. methanol, heated under reflux for 3 hours, evaporated and the residue taken up in water, extracted with dichloromethane, dried over anhydrous sodium sulphate and evaporated. After chromatography on silica gel with an elution mixture of 95% dichloromethane and 5% methanol, there are obtained 8.0 g. of the title compound (75% of theory) in the form of an oily base, the hydrochloride of which, prepared in ethyl acetate, melts at 132°-135° C.

Workup

  1. additionA mixture of 9.0 g
  2. temperatureunder reflux for 16 hours
  3. customThe reaction mixture is evaporated
  4. washwashed with dilute acetic acid and subsequently with water
  5. dry with materialdried over anhydrous sodium sulphate
  6. customevaporated
  7. additionmixed with a solution of 3.3 g
  8. temperaturemethanol, heated
  9. temperatureunder reflux for 3 hours
  10. customevaporated
  11. extractionextracted with dichloromethane
  12. dry with materialdried over anhydrous sodium sulphate
  13. customevaporated
  14. additionAfter chromatography on silica gel with an elution mixture of 95% dichloromethane and 5% methanol, there
  15. customare obtained 8.0 g

Sources & evidence

ORD record
ord-0e727cd97da94cbe94ac9d306ac5073f
Source dataset
uspto-grants-1989_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04853386

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes