HCID 23153217, compound → HCID 23153442, compound

HRID 492942Notes

Reaction equation

HRID 492942 reaction equation
[F:1][C:2]1[CH:30]=[C:29]([N+:31]([O-])=O)[CH:28]=[CH:27][C:3]=1[O:4][C:5]1[N:10]=[CH:9][N:8]=[C:7]([NH:11][C:12](=[O:26])[N:13]([CH3:25])[CH:14]2[CH2:19][CH2:18][N:17]([CH:20]3[CH2:23][N:22]([CH3:24])[CH2:21]3)[CH2:16][CH2:15]2)[CH:6]=1>O1CCCC1.[C+4].[OH-].[Pd+2].[OH-].[OH-].[OH-].[OH-].[OH-]>[NH2:31][C:29]1[CH:28]=[CH:27][C:3]([O:4][C:5]2[N:10]=[CH:9][N:8]=[C:7]([NH:11][C:12](=[O:26])[N:13]([CH3:25])[CH:14]3[CH2:15][CH2:16][N:17]([CH:20]4[CH2:21][N:22]([CH3:24])[CH2:23]4)[CH2:18][CH2:19]3)[CH:6]=2)=[C:2]([F:1])[CH:30]=1

Participants

4

Reactant 1

HCID 23153217HCID 23153217, compound

Product 1

HCID 23153442HCID 23153442, compoundYield 75.4%

Reagents, catalysts & solvents 2

HCID 178420936HCID 178420936, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-[6-(2-fluoro-4-nitrophenoxy)pyrimidin-4-yl]-1-methyl-1-[1-(1-methylazetidin-3-yl)piperidin-4-yl]urea (193 mg) in tetrahydrofuran (100 ml) was added 20% palladium hydroxide carbon (590 mg), followed by stirring under a hydrogen atmosphere at room temperature for 6.5 hrs. The reaction mixture was filtered to remove the catalyst, and the catalyst was washed with methanol. The filtrate was concentrated to provide the titled compound (136 mg, 75.4%) as pale yellow solid.

Workup

  1. filtrationThe reaction mixture was filtered
  2. customto remove the catalyst
  3. washthe catalyst was washed with methanol
  4. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-693be428b59041969862549dc142af50
Source dataset
uspto-grants-2009_05
Patent number
US07531532B2

Reaction notes

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