Allylamine → HCID 18326549, compound

HRID 1250676Notes

Reaction equation

HRID 1250676 reaction equation
[Cl:1][C:2]1[N:3]=[C:4](Cl)[C:5]2[S:10][CH:9]=[C:8]([CH2:11][CH2:12][CH3:13])[C:6]=2[N:7]=1.[CH2:15]([NH2:18])[CH:16]=[CH2:17]>CN(C=O)C>[CH2:15]([NH:18][C:4]1[C:5]2[S:10][CH:9]=[C:8]([CH2:11][CH2:12][CH3:13])[C:6]=2[N:7]=[C:2]([Cl:1])[N:3]=1)[CH:16]=[CH2:17]

Participants

4

Reactant 2

HCID 7853AllylamineHCID 18326430HCID 18326430, compound

Product 1

HCID 18326549HCID 18326549, compoundYield 60.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

In 5 ml of DMF, 371 mg (1.5 mmol) of 2,4-dichloro-7-propylthieno[3,2-d]pyrimidine was dissolved, and then 188 mg (3.3 mmol) of allylamine was added dropwise thereto under ice cooling over 5 minutes. The reaction solution was stirred at 0° C. for one hour and then allowed to resume room temperature, followed by stirring for further 1 hour. 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=1/10) to give 244 mg (yield: 60.7%) of the title compound.

Workup

  1. customto resume room temperature
  2. stirringby stirring for further 1 hour
  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=1/10)

Sources & evidence

ORD record
ord-7a4982e7046a49a19de529e62bfe824f
Source dataset
uspto-grants-2002_01
Patent number
US06339089B2

Reaction notes

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