HCID 23153574, compound → HCID 23153066, compound

HRID 492896Notes

Reaction equation

HRID 492896 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[CH:10]=[C:9]([NH:11][C:12]([N:14]2[CH2:19][CH2:18][N:17]([CH:20]3[CH2:25][CH2:24][N:23]([CH3:26])[CH2:22][CH2:21]3)[CH2:16][CH2:15]2)=[O:13])[N:8]=[CH:7][N:6]=1>O1CCCC1.[OH-].[Pd+2].[OH-].[C]>[NH2:31][C:29]1[CH:28]=[CH:27][C:3]([O:4][C:5]2[CH:10]=[C:9]([NH:11][C:12]([N:14]3[CH2:19][CH2:18][N:17]([CH:20]4[CH2:21][CH2:22][N:23]([CH3:26])[CH2:24][CH2:25]4)[CH2:16][CH2:15]3)=[O:13])[N:8]=[CH:7][N:6]=2)=[C:2]([F:1])[CH:30]=1

Participants

4

Reactant 1

HCID 23153574HCID 23153574, compound

Product 1

HCID 23153066HCID 23153066, compoundYield 99%

Reagents, catalysts & solvents 2

HCID 178502593HCID 178502593, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

4-(2-Fluoro-4-nitrophenoxy)-6-{[4-(1-methylpiperidin-4-yl)piperazin-1-yl]carbonylamino}pyrimidine (145 mg) was dissolved in tetrahydrofuran (20 ml). After adding 20% palladium hydroxide-carbon (100 mg), the mixture was stirred overnight under a hydrogen atmosphere. The catalyst was filtered and washed with tetrahydrofuran. The filtrate and the washings were combined and concentrated under reduced pressure, and the resultant residue was dried under reduced pressure to provide the title compound (134 mg, 99%) as a pale yellow oil.

Workup

  1. filtrationThe catalyst was filtered
  2. washwashed with tetrahydrofuran
  3. concentrationconcentrated under reduced pressure
  4. dry with materialthe resultant residue was dried under reduced pressure

Sources & evidence

ORD record
ord-98ea5f6c0e59428089f8ff9947222b78
Source dataset
uspto-grants-2009_05
Patent number
US07531532B2

Reaction notes

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