HCID 23153573, compound → HCID 23153122, compound

HRID 492871Notes

Reaction equation

HRID 492871 reaction equation
[CH3:1][N:2]([CH3:31])[CH2:3][CH2:4][N:5]1[CH2:10][CH2:9][N:8]([C:11]([NH:13][C:14]2[CH:19]=[C:18]([O:20][C:21]3[CH:26]=[CH:25][C:24]([N+:27]([O-])=O)=[CH:23][C:22]=3[F:30])[N:17]=[CH:16][N:15]=2)=[O:12])[CH2:7][CH2:6]1>O1CCCC1.[OH-].[Pd+2].[OH-].[C]>[NH2:27][C:24]1[CH:25]=[CH:26][C:21]([O:20][C:18]2[CH:19]=[C:14]([NH:13][C:11]([N:8]3[CH2:9][CH2:10][N:5]([CH2:4][CH2:3][N:2]([CH3:31])[CH3:1])[CH2:6][CH2:7]3)=[O:12])[N:15]=[CH:16][N:17]=2)=[C:22]([F:30])[CH:23]=1

Participants

4

Reactant 1

HCID 23153573HCID 23153573, compound

Product 1

HCID 23153122HCID 23153122, compoundYield 97%

Reagents, catalysts & solvents 2

HCID 178502593HCID 178502593, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

4-{[4-(2-Dimethylaminoethyl)piperazin-1-yl]carbonylamino}-6-(2-fluoro-4-nitrophenoxy)pyrimidine (167 mg) was dissolved in tetrahydrofuran (16 ml). After adding 20% palladium hydroxide-carbon (108 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 (150 mg, 97%) as pale yellow powder.

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-563123b12f58413190b184e573a0b6f7
Source dataset
uspto-grants-2009_05
Patent number
US07531532B2

Reaction notes

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