2,4-Dichloro-6-methylpyrimidin-5-amine → 2-Chloro-4-methylpyrimidin-5-amine

HRID 2063473Notes

Reaction equation

HRID 2063473 reaction equation
[Cl:1][C:2]1[N:7]=[C:6](Cl)[C:5]([NH2:9])=[C:4]([CH3:10])[N:3]=1>CCO.O.[Pd]>[Cl:1][C:2]1[N:3]=[C:4]([CH3:10])[C:5]([NH2:9])=[CH:6][N:7]=1

Participants

5

Reactant 1

HCID 146659712,4-Dichloro-6-methylpyrimidin-5-amine

Product 1

HCID 3162822-Chloro-4-methylpyrimidin-5-amineYield 20%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

2,4-Dichloro-6-methylpyrimidin-5-amine (1.0 g, 5.62 mmol) was dissolved in anhydrous EtOH (3.5 mL) and H2O (7.0 mL). MgO (1.40 g, 34.74 mmol) and 10% Pd/C (35 mg) were added to the reaction mixture which was hydrogenated at 1 atm, at room temperature, overnight. The reaction mixture was filtered and concentrated. The residue was purified by silica gel column chromatography (MeOH/CH2Cl2 gradient, 0-15% MeOH) to afford 2-chloro-4-methylpyrimidin-5-amine as light pink solid (0.16 g, 20%).

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationconcentrated
  3. customThe residue was purified by silica gel column chromatography (MeOH/CH2Cl2 gradient, 0-15% MeOH)

Sources & evidence

ORD record
ord-5f790f68bee447d3a93a5fc537da7879
Source dataset
uspto-grants-2012_10
Patent number
US08288371B2

Reaction notes

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