4-(5-(Benzyloxy)-6-p-tolylpyrimidin-4-ylamino)-2-fluorobenzonitrile → 2-Fluoro-4-(5-hydroxy-6-p-tolylpyrimidin-4-ylamino)benzonitrile

HRID 1912648Notes

Reaction equation

HRID 1912648 reaction equation
C([O:8][C:9]1[C:10]([NH:22][C:23]2[CH:30]=[CH:29][C:26]([C:27]#[N:28])=[C:25]([F:31])[CH:24]=2)=[N:11][CH:12]=[N:13][C:14]=1[C:15]1[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][CH:16]=1)C1C=CC=CC=1>CO.C1COCC1.[Pd]>[F:31][C:25]1[CH:24]=[C:23]([NH:22][C:10]2[C:9]([OH:8])=[C:14]([C:15]3[CH:16]=[CH:17][C:18]([CH3:21])=[CH:19][CH:20]=3)[N:13]=[CH:12][N:11]=2)[CH:30]=[CH:29][C:26]=1[C:27]#[N:28]

Participants

4

Reactant 1

HCID 669583574-(5-(Benzyloxy)-6-p-tolylpyrimidin-4-ylamino)-2-fluorobenzonitrile

Product 1

HCID 669583392-Fluoro-4-(5-hydroxy-6-p-tolylpyrimidin-4-ylamino)benzonitrileYield 85.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21899815MeOH tetrahydrofuranSolvent

Procedure

The compound from step 5 (0.3 g, 0.73 mmol) was dissolved in (3:1) MeOH/THF (7.3 ml), 10% Palladium on carbon (30 mg) was added and the mixture placed under H2 (1 atm). After 1 hour LCMS showed that the reaction was complete, the catalyst was removed by filtration and the mixture concentrated to give 200 mg of the title compound. LCMS=321.2 (MH+)

Workup

  1. customthe catalyst was removed by filtration
  2. concentrationthe mixture concentrated

Sources & evidence

ORD record
ord-1b915da03a514288b5a97df4c68c97e4
Source dataset
uspto-grants-2013_12
Patent number
US08609676B2

Reaction notes

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