3-[6-(2-Fluoro-4-nitrophenoxy)pyrimidin-4-yl]-1-[1-(2-dimethylaminoethyl)piperidin-4-yl]-1-methylurea → 3-[6-(4-Amino-2-fluorophenoxy)pyrimidin-4-yl]-1-[1-(2-dimethylaminoethyl)piperidin-4-yl]-1-methylurea

HRID 492879Notes

Reaction equation

HRID 492879 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]([CH:15]2[CH2:20][CH2:19][N:18]([CH2:21][CH2:22][N:23]([CH3:25])[CH3:24])[CH2:17][CH2:16]2)[CH3:14])[CH:6]=1>O1CCCC1.[OH-].[Pd+2].[OH-].[C]>[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]([CH:15]3[CH2:20][CH2:19][N:18]([CH2:21][CH2:22][N:23]([CH3:25])[CH3:24])[CH2:17][CH2:16]3)[CH3:14])[CH:6]=2)=[C:2]([F:1])[CH:30]=1

Participants

4

Reactant 1

HCID 231532113-[6-(2-Fluoro-4-nitrophenoxy)pyrimidin-4-yl]-1-[1-(2-dimethylaminoethyl)piperidin-4-yl]-1-methylurea

Product 1

HCID 231530283-[6-(4-Amino-2-fluorophenoxy)pyrimidin-4-yl]-1-[1-(2-dimethylaminoethyl)piperidin-4-yl]-1-methylureaYield 98%

Reagents, catalysts & solvents 2

HCID 178502593HCID 178502593, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

After adding 20% palladium hydroxide-carbon (18.3 mg) to a solution of 3-[6-(2-fluoro-4-nitrophenoxy)pyrimidin-4-yl]-1-[1-(2-dimethylaminoethyl)piperidin-4-yl]-1-methylurea (240 mg) in tetrahydrofuran (10 ml), the mixture was stirred for 15.5 hours at room temperature under a hydrogen atmosphere. The catalyst was filtered and washed with methanol. The filtrate was then concentrated to provide the title compound (220 mg, 98.0%) as a yellow amorphous substance.

Workup

  1. filtrationThe catalyst was filtered
  2. washwashed with methanol
  3. concentrationThe filtrate was then concentrated

Sources & evidence

ORD record
ord-2ec235e084a94105b7be20c431864556
Source dataset
uspto-grants-2009_05
Patent number
US07531532B2

Reaction notes

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