Sodium hydride → (6-Chloropyrimidin-4-yl)-(2-methylquinolin-4-yl)amine

HRID 914997Notes

Reaction equation

HRID 914997 reaction equation
[NH2:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[C:4]([CH3:12])[CH:3]=1.[H-].[Na+].[Cl:15][C:16]1[CH:21]=[C:20](Cl)[N:19]=[CH:18][N:17]=1>CN(C=O)C>[Cl:15][C:16]1[N:17]=[CH:18][N:19]=[C:20]([NH:1][C:2]2[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[N:5]=[C:4]([CH3:12])[CH:3]=2)[CH:21]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 709434,6-DichloropyrimidineHCID 811164-Amino-2-methylquinoline

Product 1

HCID 58958180(6-Chloropyrimidin-4-yl)-(2-methylquinolin-4-yl)amineYield 5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of 4-amino-2-methylquinoline (107) (1.0 g, 6.7 mmol) in anhydrous DMF (60 mL) was added NaH (60% in mineral oil, 0.32 g, 8.0 mmol). The mixture was stirred for 1 hour followed by the addition of 4,6-dichloropyrimidine (106) (1.0 g, 6.7 mmol). The reaction was heated at 90° C. overnight before it was poured into ice water (100 mL). The mixture was extracted with ether (3×100 mL) and the combined organic layers were dried (MgSO4), concentrated under reduced pressure. The residue was purified by flash chromatrography (SiO2, gradient elution, hexanes to 3:1 hexanes/ethyl acetate to 7:3 CH2Cl2/MeOH) to provide 108 (80 mg, 5%) as a white solid.

Workup

  1. extractionThe mixture was extracted with ether (3×100 mL)
  2. dry with materialthe combined organic layers were dried (MgSO4)
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by flash chromatrography (SiO2, gradient elution, hexanes to 3:1 hexanes/ethyl acetate to 7:3 CH2Cl2/MeOH)

Sources & evidence

ORD record
ord-11a344c2a6a148d1a722aa075575aa94
Source dataset
uspto-grants-2007_09
Patent number
US07265122B2

Reaction notes

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