HCID 23153485, compound → HCID 23153632, compound

HRID 492857Notes

Reaction equation

HRID 492857 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([O:8][C:9]2[CH:14]=[C:13]([NH:15][C:16]([N:18]([CH3:26])[CH:19]3[CH2:24][CH2:23][N:22]([CH3:25])[CH2:21][CH2:20]3)=[O:17])[N:12]=[CH:11][N:10]=2)[CH:5]=[CH:4][C:3]=1[NH:27]C(=O)OCC1C=CC=CC=1>O1CCCC1.[OH-].[Pd+2].[OH-].[C]>[NH2:27][C:3]1[CH:4]=[CH:5][C:6]([O:8][C:9]2[N:10]=[CH:11][N:12]=[C:13]([NH:15][C:16](=[O:17])[N:18]([CH3:26])[CH:19]3[CH2:24][CH2:23][N:22]([CH3:25])[CH2:21][CH2:20]3)[CH:14]=2)=[CH:7][C:2]=1[F:1]

Participants

4

Reactant 1

HCID 23153485HCID 23153485, compound

Product 1

HCID 23153632HCID 23153632, compound

Reagents, catalysts & solvents 2

HCID 178502593HCID 178502593, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

Benzyl N-(2-fluoro-4-{6-[3-methyl-3-(1-methylpiperidin-4-yl)ureido]pyrimidin-4-yloxy}phenyl)carbamate (189 mg) was dissolved in tetrahydrofuran (20 ml). After adding 20% palladium hydroxide-carbon (104 mg), the mixture was stirred for 10 hours under a hydrogen atmosphere. The catalyst was filtered and washed with ethyl acetate. The filtrate and the washings were combined and concentrated under reduced pressure to provide crude 3-[6-(4-amino-3-fluorophenoxy)pyrimidin-4-yl]-1-methyl-1-(1-methylpiperidin-4-yl)urea as a colorless oil [ESI-MS (m/z): 375[M+H]+].

Workup

  1. filtrationThe catalyst was filtered
  2. washwashed with ethyl acetate
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-2d148092915f4125b2c82c4cb0766499
Source dataset
uspto-grants-2009_05
Patent number
US07531532B2

Reaction notes

Loading…