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

HRID 1926816Notes

Reaction equation

HRID 1926816 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-bf498af55a064b6898cc2a4722fe4026
Source dataset
uspto-grants-2012_05
Patent number
US08183241B2

Reaction notes

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