Sodium hydride → 4-(5-(Benzyloxy)-6-p-tolylpyrimidin-4-ylamino)-2-fluorobenzonitrile

HRID 1912647Notes

Reaction equation

HRID 1912647 reaction equation
[CH2:1]([O:8][C:9]1[C:10](Cl)=[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)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:23]([C:25]1[CH:31]=[CH:30][C:28]([NH2:29])=[CH:27][C:26]=1[F:32])#[N:24].[H-].[Na+]>CN(C=O)C>[CH2:1]([O:8][C:9]1[C:10]([NH:29][C:28]2[CH:30]=[CH:31][C:25]([C:23]#[N:24])=[C:26]([F:32])[CH:27]=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)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 27834134-Amino-2-fluorobenzonitrileHCID 866659375-(Benzyloxy)-4-chloro-6-p-tolylpyrimidine

Product 1

HCID 669583574-(5-(Benzyloxy)-6-p-tolylpyrimidin-4-ylamino)-2-fluorobenzonitrileYield 76.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The compound from step 4 (0.3 g, 0.96 mmol) was dissolved in DMF (4.83 ml), 4-cyano-3-fluoroaniline (0.131 g, 1 eq) and NaH (0.155 g of 60% dispersion in mineral oil, 4 eq) were added. After 1 hour LCMS showed complete conversion, the reaction was quenched with NH4Cl(sat) and extracted with EtOAc. The extracts were dried concentrated and the residue purified by silica gel chromatography (0-20% EtOAc in hexane) to give 0.3 g of the title compound.

Workup

  1. customconversion, the reaction was quenched with NH4Cl(sat)
  2. extractionextracted with EtOAc
  3. customThe extracts were dried
  4. concentrationconcentrated
  5. customthe residue purified by silica gel chromatography (0-20% EtOAc in hexane)

Sources & evidence

ORD record
ord-3ac2c0115ee04a3dbd1dc7652f949ebd
Source dataset
uspto-grants-2013_12
Patent number
US08609676B2

Reaction notes

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