Methanol → 1-[(6-amino-9H-purin-9-yl)methyl]-4-propylpyrrolidin-2-one

HRID 1924242Notes

Reaction equation

HRID 1924242 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].C([O-])=O.[NH4+:24].C1COCC1.CO>[Pd].C(Cl)Cl.CCCCCC>[NH2:24][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]

Participants

8

Reactant 4

HCID 887MethanolHCID 8028TetrahydrofuranHCID 2723923Ammonium formateHCID 577430091-[(6-chloro-9H-purin-9-yl)methyl]-4-propylpyrrolidin-2-one

Product 1

HCID 577430991-[(6-amino-9H-purin-9-yl)methyl]-4-propylpyrrolidin-2-oneYield 60%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 6344DichloromethaneSolventHCID 8058HexaneSolvent

Procedure

A solution of intermediate x75 (600 mg, 2.04 mmol), ammonium formiate (644 mg, 5 eq, 10.21 mmol) and palladium on charcoal (10% wt, 109 mg, 0.1 mmol) in a 1 to 1 mixture of THF and methanol (20 ml) is allowed to react at ambient temperature for 16 hours. After filtration on celite and solvent evaporation, the crude product is purified using preparative chromatography on silicagel to furnish a crude compound which is recristallized in a mixture of CH2Cl2 and hexane to furnish 1-[(6-amino-9H-purin-9-yl)methyl]-4-propylpyrrolidin-2-one 283 as a white crystalline product (320 mg).

Workup

  1. customto react at ambient temperature for 16 hours
  2. filtrationAfter filtration
  3. customon celite and solvent evaporation
  4. customthe crude product is purified
  5. customto furnish a crude compound which

Sources & evidence

ORD record
ord-4a3202c27cfa4072b4ca8fed789fef81
Source dataset
uspto-grants-2012_05
Patent number
US08178533B2

Reaction notes

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