Allylamine → HCID 18326530, compound

HRID 1250673Notes

Reaction equation

HRID 1250673 reaction equation
[Cl:1][C:2]1[N:3]=[C:4](Cl)[C:5]2[S:10][CH:9]=[C:8]([CH2:11][CH3:12])[C:6]=2[N:7]=1.[CH2:14]([NH2:17])[CH:15]=[CH2:16]>CN(C=O)C>[CH2:14]([NH:17][C:4]1[C:5]2[S:10][CH:9]=[C:8]([CH2:11][CH3:12])[C:6]=2[N:7]=[C:2]([Cl:1])[N:3]=1)[CH:15]=[CH2:16]

Participants

4

Reactant 2

HCID 7853AllylamineHCID 18326507HCID 18326507, compound

Product 1

HCID 18326530HCID 18326530, compoundYield 90.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

In 6 ml of DMF, 500 mg (2.1 mmol) of 2,4-dichloro-7-etylthieno[3,2-d]pyrimidine was dissolved, and then 269 mg (4.7 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 483 mg (yield: 88.8%) 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-988f08d9255a4e5aa6ad4f5df3d9e1a7
Source dataset
uspto-grants-2002_01
Patent number
US06339089B2

Reaction notes

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