3-[5-(2-Methylsulfanyl-pyrimidin-4-yl)-thiophen-2-yl]-4-nitro-butyric acid methyl ester → 4-[5-(2-Methylsulfanyl-pyrimidin-4-yl)-thiophen-2-yl]-pyrrolidin-2-one

HRID 1434924Notes

Reaction equation

HRID 1434924 reaction equation
C[O:2][C:3](=O)[CH2:4][CH:5]([C:10]1[S:11][C:12]([C:15]2[CH:20]=[CH:19][N:18]=[C:17]([S:21][CH3:22])[N:16]=2)=[CH:13][CH:14]=1)[CH2:6][N+:7]([O-])=O>C(O)C.[Ni]>[CH3:22][S:21][C:17]1[N:16]=[C:15]([C:12]2[S:11][C:10]([CH:5]3[CH2:6][NH:7][C:3](=[O:2])[CH2:4]3)=[CH:14][CH:13]=2)[CH:20]=[CH:19][N:18]=1

Participants

4

Reactant 1

HCID 579361643-[5-(2-Methylsulfanyl-pyrimidin-4-yl)-thiophen-2-yl]-4-nitro-butyric acid methyl ester

Product 1

HCID 579363254-[5-(2-Methylsulfanyl-pyrimidin-4-yl)-thiophen-2-yl]-pyrrolidin-2-one

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 935NickelSolvent

Procedure

The nitro derivative from Step B (100 mg, 0.283 mmol) was dissolved in 10 ml of ethanol and hydrogenated with Raney-nickel for 18 hours. The catalyst was then filtered off and the solution was heated to reflux for 3 hours. After evaporation, the crude product was purified by preparative HPLC. Yield: 19 mg (23%).

Workup

  1. filtrationThe catalyst was then filtered off
  2. temperaturethe solution was heated
  3. temperatureto reflux for 3 hours
  4. customAfter evaporation
  5. customthe crude product was purified by preparative HPLC

Sources & evidence

ORD record
ord-85991da404c9422783fe717c288969a8
Source dataset
uspto-grants-2009_11
Patent number
US07615562B2

Reaction notes

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