Cyclopropylamine → 1-([6-(cyclopropylamino)-9H-purin-9-yl]methyl}-4-propylpyrrolidin-2-one

HRID 2043665Notes

Reaction equation

HRID 2043665 reaction equation
Cl[C:2]1[N:10]=[CH:9][N:8]=[C:7]2[C:3]=1[N:4]=[CH:5][N:6]2[CH2:11][N:12]1[CH2:16][CH:15]([CH2:17][CH2:18][CH3:19])[CH2:14][C:13]1=[O:20].[CH:21]1([NH2:24])[CH2:23][CH2:22]1.C([O-])(O)=O.[Na+]>C1COCC1>[CH:21]1([NH:24][C:2]2[N:10]=[CH:9][N:8]=[C:7]3[C:3]=2[N:4]=[CH:5][N:6]3[CH2:11][N:12]2[CH2:16][CH:15]([CH2:17][CH2:18][CH3:19])[CH2:14][C:13]2=[O:20])[CH2:23][CH2:22]1

Participants

5

Reactant 3

HCID 69828CyclopropylamineHCID 516892Sodium BicarbonateHCID 577430091-[(6-chloro-9H-purin-9-yl)methyl]-4-propylpyrrolidin-2-one

Product 1

HCID 159799161-([6-(cyclopropylamino)-9H-purin-9-yl]methyl}-4-propylpyrrolidin-2-oneYield 54%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 1-[(6-chloro-9H-purin-9-yl)methyl]-4-propylpyrrolidin-2-one x166 (250 mg, 0.85 mmol, 1 eq) and cyclopropylamine (1 ml) is heated at 50° C. during 24 hours in THF. After cooling, a saturated aqueous solution of NaHCO3 is added and the aqueous phase is extracted with AcOEt. The combined organic layers are dried on anhydrous MgSO4, filtered of and evaporated under reduced pressure. The crude mixture is purified by preparative HPLC to yield 1-{[6-(cyclopropylamino)-9H-purin-9-yl]methyl}-4-propylpyrrolidin-2-one 285.

Workup

  1. temperatureAfter cooling
  2. extractionthe aqueous phase is extracted with AcOEt
  3. dry with materialThe combined organic layers are dried on anhydrous MgSO4
  4. filtrationfiltered of and
  5. customevaporated under reduced pressure
  6. customThe crude mixture is purified by preparative HPLC

Sources & evidence

ORD record
ord-9a54a5455ba94db98e24bf2ceeeb6e05
Source dataset
uspto-grants-2013_11
Patent number
US08586623B2

Reaction notes

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