Allylamine → 4-Allylamino-7-bromo-2-chlorothieno[3,2-d]pyrimidine

HRID 1250689Notes

Reaction equation

HRID 1250689 reaction equation
[Br:1][C:2]1[C:6]2[N:7]=[C:8]([Cl:12])[N:9]=[C:10](Cl)[C:5]=2[S:4][CH:3]=1.[CH2:13]([NH2:16])[CH:14]=[CH2:15]>CN(C=O)C>[CH2:13]([NH:16][C:10]1[C:5]2[S:4][CH:3]=[C:2]([Br:1])[C:6]=2[N:7]=[C:8]([Cl:12])[N:9]=1)[CH:14]=[CH2:15]

Participants

4

Reactant 2

HCID 7853AllylamineHCID 183264227-Bromo-2,4-dichlorothieno[3,2-d]pyrimidine

Product 1

HCID 183264694-Allylamino-7-bromo-2-chlorothieno[3,2-d]pyrimidineYield 78.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To 5 ml of a solution of 426 mg (1.5 mmol) of 7-bromo-2,4-dichlorothieno[3,2-d]pyrimidine in DMF was added 188 mg (3.3 mmol) of allylamine 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 1 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 359 mg (yield: 78.6%) of the title compound.

Workup

  1. customto resume room temperature
  2. stirringby stirring for further 1 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-644e2661d3274309aea22ce67d4a15f1
Source dataset
uspto-grants-2002_01
Patent number
US06339089B2

Reaction notes

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