Water → (2-Chloro-pyrimidin-4-yl)-methyl-quinolin-3-yl-amine

HRID 495462Notes

Reaction equation

HRID 495462 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([NH:8][C:9]2[CH:10]=[N:11][C:12]3[C:17]([CH:18]=2)=[CH:16][CH:15]=[CH:14][CH:13]=3)[CH:5]=[CH:4][N:3]=1.[CH3:19]I.[H-].[Na+].O>CN(C=O)C>[Cl:1][C:2]1[N:7]=[C:6]([N:8]([CH3:19])[C:9]2[CH:10]=[N:11][C:12]3[C:17]([CH:18]=2)=[CH:16][CH:15]=[CH:14][CH:13]=3)[CH:5]=[CH:4][N:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 22326846(2-Chloropyrimidin-4-yl)quinolin-3-ylamine

Product 1

HCID 22326843(2-Chloro-pyrimidin-4-yl)-methyl-quinolin-3-yl-amine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of (2-chloro-pyrimidin-4-yl)-quinolin-3-yl-amine (0.400 g, 1.64 mmol) in DMF (7 mL) at 0° C. was added MeI (0.133 mL, 2.13 mmol) and NaH (60% dispersion in mineral oil, 0.079 g, 1.97 mmol). The reaction mixture was warmed to RT, accompanied by the appearance of a yellow color and solid precipitate. After stirring for 1 h at RT, H2O (25 mL) was added and the mixture was extracted with EtOAc (3×10 mL). The combined organic layers were washed with brine, dried with MgSO4, filtered and concentrated under reduced pressure. Chromatography on silica gel (1:1 EtOAc:Hexanes) provided the title compound.

Workup

  1. extractionthe mixture was extracted with EtOAc (3×10 mL)
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried with MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-83a084a4d5654287a2da1f0af506acc7
Source dataset
uspto-grants-2005_09
Patent number
US06939874B2

Reaction notes

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