Methylamine → HCID 22648746, compound

HRID 393164Notes

Reaction equation

HRID 393164 reaction equation
CS(O[CH:6]([C:10]1[C:11]([CH:16]([CH3:18])[CH3:17])=[N:12][CH:13]=[N:14][CH:15]=1)[CH:7]([CH3:9])[CH3:8])(=O)=O.[CH3:19][NH2:20]>C(O)(C)C>[CH3:19][NH:20][CH:6]([C:10]1[C:11]([CH:16]([CH3:18])[CH3:17])=[N:12][CH:13]=[N:14][CH:15]=1)[CH:7]([CH3:9])[CH3:8]

Participants

4

Reactant 2

HCID 6329MethylamineHCID 22648759HCID 22648759, compound

Product 1

HCID 22648746HCID 22648746, compoundYield 36%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

10.6 g (39 mmol) of 5-(1-methylsulfonyloxy-2-methylpropyl)-4-isopropylpyrimidine was dissolved in 50 ml of isopropyl alcohol, and 10 ml (129 mmol) of a 40% methylamine aqueous solution was added, followed by stirring at room temperature for 8 hours. After completion of the reaction, the solvent was distilled off under reduced pressure, and 100 ml of water was added, followed by extraction with ethyl acetate. The obtained organic layer was washed with water and then dried over anhydrous magnesium sulfate. Ethyl acetate was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography (developing solvent=ethyl acetate) to obtain 2.9 g (yield: 36%) of 5-[1-(N-methylamino)-2-methylpropyl]-4-isopropylpyrimidine as slightly yellow crystals (melting point: 37-39° C.).

Workup

  1. customAfter completion of the reaction
  2. distillationthe solvent was distilled off under reduced pressure, and 100 ml of water
  3. additionwas added
  4. extractionfollowed by extraction with ethyl acetate
  5. washThe obtained organic layer was washed with water
  6. dry with materialdried over anhydrous magnesium sulfate
  7. distillationEthyl acetate was distilled off under reduced pressure
  8. customthe residue was purified by silica gel column chromatography (developing solvent=ethyl acetate)

Sources & evidence

ORD record
ord-1985612f2ddf478284f7157890b35a4e
Source dataset
uspto-grants-2004_10
Patent number
US06806230B1

Reaction notes

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