HCID 57677448, compound → HCID 57677561, compound

HRID 492867Notes

Reaction equation

HRID 492867 reaction equation
[CH3:1][N:2]([CH2:4][C@@H:5]1[CH2:9][CH2:8][N:7]([C:10]([NH:12][C:13]2[CH:18]=[C:17]([O:19][C:20]3[CH:25]=[CH:24][C:23]([N+:26]([O-])=O)=[CH:22][C:21]=3[F:29])[N:16]=[CH:15][N:14]=2)=[O:11])[CH2:6]1)[CH3:3]>O1CCCC1.[OH-].[Pd+2].[OH-].[C]>[NH2:26][C:23]1[CH:24]=[CH:25][C:20]([O:19][C:17]2[CH:18]=[C:13]([NH:12][C:10]([N:7]3[CH2:8][CH2:9][C@@H:5]([CH2:4][N:2]([CH3:3])[CH3:1])[CH2:6]3)=[O:11])[N:14]=[CH:15][N:16]=2)=[C:21]([F:29])[CH:22]=1

Participants

4

Reactant 1

HCID 57677448HCID 57677448, compound

Product 1

HCID 57677561HCID 57677561, compoundYield 91.5%

Reagents, catalysts & solvents 2

HCID 178502593HCID 178502593, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

4-{[(3S)-3-(Dimethylaminomethyl)pyrrolidin-1-yl]carbonylamino}-6-(2-fluoro-4-nitrophenoxy)pyrimidine (124 mg) was dissolved in tetrahydrofuran (15 ml). After adding 20% palladium hydroxide-carbon (86 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 then the resultant residue was dried under reduced pressure to provide the title compound (105 mg, 91%) 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-b2f75386fd4743c29e2e778213a58e64
Source dataset
uspto-grants-2009_05
Patent number
US07531532B2

Reaction notes

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