4-(1-Methylazetidin-3-yl)piperazine-1-carboxylic acid [6-(2-fluoro-4-nitrophenoxy)pyrimidin-4-yl]amide → 4-(1-Methylazetidin-3-yl)piperazine-1-carboxylic acid [6-(4-amino-2-fluorophenoxy)pyrimidin-4-yl]amide

HRID 492903Notes

Reaction equation

HRID 492903 reaction equation
[F:1][C:2]1[CH:28]=[C:27]([N+:29]([O-])=O)[CH:26]=[CH:25][C:3]=1[O:4][C:5]1[N:10]=[CH:9][N:8]=[C:7]([NH:11][C:12]([N: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)=[O:13])[CH:6]=1>O1CCCC1.[OH-].[Pd+2].[OH-]>[NH2:29][C:27]1[CH:26]=[CH:25][C:3]([O:4][C:5]2[N:10]=[CH:9][N:8]=[C:7]([NH:11][C:12]([N:14]3[CH2:15][CH2:16][N:17]([CH:20]4[CH2:23][N:22]([CH3:24])[CH2:21]4)[CH2:18][CH2:19]3)=[O:13])[CH:6]=2)=[C:2]([F:1])[CH:28]=1

Participants

4

Reactant 1

HCID 576773444-(1-Methylazetidin-3-yl)piperazine-1-carboxylic acid [6-(2-fluoro-4-nitrophenoxy)pyrimidin-4-yl]amide

Product 1

HCID 576776494-(1-Methylazetidin-3-yl)piperazine-1-carboxylic acid [6-(4-amino-2-fluorophenoxy)pyrimidin-4-yl]amideYield 64.2%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

After adding 20% palladium hydroxide (150 mg) to a solution of 4-(1-methylazetidin-3-yl)piperazine-1-carboxylic acid [6-(2-fluoro-4-nitrophenoxy)pyrimidin-4-yl]amide (69.1 mg) in tetrahydrofuran, the mixture was stirred for 7 hours at room temperature under a hydrogen atmosphere. The catalyst was then filtered. The filtrate was concentrated to provide the title compound (31.8 mg, 64.2%) as a yellow oil.

Workup

  1. filtrationThe catalyst was then filtered
  2. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-6eea1b4789e34eb5810f67b7b9c9770d
Source dataset
uspto-grants-2009_05
Patent number
US07531532B2

Reaction notes

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