Triethylamine → HCID 18326416, compound

HRID 1250669Notes

Reaction equation

HRID 1250669 reaction equation
[Cl:1][C:2]1[N:3]=[C:4](Cl)[C:5]2[S:10][CH:9]=[C:8]([CH3:11])[C:6]=2[N:7]=1.C(N(CC)CC)C.Cl.[CH3:21][C:22]([CH3:26])=[CH:23][CH2:24][NH2:25]>CN(C=O)C>[Cl:1][C:2]1[N:3]=[C:4]([NH:25][CH2:24][CH:23]=[C:22]([CH3:26])[CH3:21])[C:5]2[S:10][CH:9]=[C:8]([CH3:11])[C:6]=2[N:7]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 71470642,4-Dichloro-7-methylthieno(3,2-d)pyrimidineHCID 183265643-Methylbut-2-en-1-amine hydrochloride

Product 1

HCID 18326416HCID 18326416, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To 10 ml of a solution of 438 mg (2.0 mmol) of 2,4-dichloro-7-metylthieno[3,2-d]pyrimidine and 445 mg (4.4 mmol) of triethylamine in DMF was added 243 mg (2.0 mmol) of 3-methyl-2-butenylamine hydrochloride 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=1/4) to give 396 mg (yield: 74.0%) 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=1/4)

Sources & evidence

ORD record
ord-b62227390d1943b0a44283c383fc09f3
Source dataset
uspto-grants-2002_01
Patent number
US06339089B2

Reaction notes

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