4-(2-Fluoro-4-nitrophenoxy)-6-{[4-(1-methylpiperazin-4-yl)piperidin-1-yl]carbonylamino}pyrimidine → 4-(4-Amino-2-fluorophenoxy)-6-{[4-(1-methylpiperazin-4-yl)piperidin-1-yl]carbonylamino}pyrimidine

HRID 492894Notes

Reaction equation

HRID 492894 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][CH:17]([N: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][CH:17]([N: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 231535264-(2-Fluoro-4-nitrophenoxy)-6-{[4-(1-methylpiperazin-4-yl)piperidin-1-yl]carbonylamino}pyrimidine

Product 1

HCID 231531584-(4-Amino-2-fluorophenoxy)-6-{[4-(1-methylpiperazin-4-yl)piperidin-1-yl]carbonylamino}pyrimidineYield 100.8%

Reagents, catalysts & solvents 2

HCID 178502593HCID 178502593, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

4-(2-Fluoro-4-nitrophenoxy)-6-{[4-(1-methylpiperazin-4-yl)piperidin-1-yl]carbonylamino}pyrimidine (104 mg) was dissolved in tetrahydrofuran (15 ml). After adding 20% palladium hydroxide-carbon (70 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 (98 mg, quantitative) 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-b898e653263e496f9cdda6bd2f6bf0af
Source dataset
uspto-grants-2009_05
Patent number
US07531532B2

Reaction notes

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