Methylamine → HCID 15908145, compound

HRID 1250684Notes

Reaction equation

HRID 1250684 reaction equation
[Cl:1][C:2]1[N:3]=[C:4](Cl)[C:5]2[S:10][CH:9]=[C:8]([CH:11]([CH3:13])[CH3:12])[C:6]=2[N:7]=1.[CH3:15][NH2:16]>CN(C=O)C.CO>[Cl:1][C:2]1[N:3]=[C:4]([NH:16][CH3:15])[C:5]2[S:10][CH:9]=[C:8]([CH:11]([CH3:13])[CH3:12])[C:6]=2[N:7]=1

Participants

5

Reactant 2

HCID 6329MethylamineHCID 15908142HCID 15908142, compound

Product 1

HCID 15908145HCID 15908145, compoundYield 92%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Procedure

To 10 ml of a solution of 100 mg (0.41 mmol) of 2,4-dichloro-7-isopropylthieno[3,2-d]pyrimidine in DMF was added 40% methylamine solution in methanol under ice cooling. The reaction mixture was stirred at the same temperature for one hour and then allowed to resume room temperature, followed by stirring for further 2 hours. After completion of the reaction, ice water was added to the reaction mixture, followed by extraction with ethyl acetate (50 ml×3). After the organic layer was washed successively with 1N hydrochloric acid, water and brine and dried over anhydrous sodium sulfate, the solvent was distilled off under reduced pressure. The residue was purified by silica gel chromatography (eluent: ethyl acetate-hexane=1/2) to give 90 mg (yield: 92.0%) of the title compound.

Workup

  1. customto resume room temperature
  2. stirringby stirring for further 2 hours
  3. additionwas added to the reaction mixture
  4. extractionfollowed by extraction with ethyl acetate (50 ml×3)
  5. washAfter the organic layer was washed successively with 1N hydrochloric acid, water and brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. distillationthe solvent was distilled off under reduced pressure
  8. customThe residue was purified by silica gel chromatography (eluent: ethyl acetate-hexane=1/2)

Sources & evidence

ORD record
ord-613de8bebc4b4a1d825674f17a3e39ff
Source dataset
uspto-grants-2002_01
Patent number
US06339089B2

Reaction notes

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