Allylamine → HCID 18326528, compound

HRID 1250622Notes

Reaction equation

HRID 1250622 reaction equation
[CH2:1]([NH2:4])[CH:2]=[CH2:3].[C:5]([NH:9][C:10]1[C:11]2[S:19][CH:18]=[C:17]([CH3:20])[C:12]=2[N:13]=[C:14](Cl)[N:15]=1)([CH3:8])([CH3:7])[CH3:6]>O>[CH2:1]([NH:4][C:14]1[N:15]=[C:10]([NH:9][C:5]([CH3:8])([CH3:7])[CH3:6])[C:11]2[S:19][CH:18]=[C:17]([CH3:20])[C:12]=2[N:13]=1)[CH:2]=[CH2:3]

Participants

4

Reactant 2

HCID 7853AllylamineHCID 18326429HCID 18326429, compound

Product 1

HCID 18326528HCID 18326528, compoundYield 91.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
140 °C

Procedure

In 2.28 g (40.0 mmol) of allylamine was dissolved 250 mg (1.0 mmol) of 4-t-butylamino-2-chloro-7-methylthieno[3,2-d]pyrimidine, and the resulting solution was heated in a sealed tube at 140° C. for 24 hours. After the reaction mixture was cooled, 100 ml of water was added thereto, followed by extraction with ethyl acetate (20 ml×3). The organic layer was washed with 20 ml of water and dried over anhydrous sodium sulfate, and then the solvent was distilled off. The residue was purified by silica gel column chromatography (eluent: ethyl acetate-hexane=1/4) to give 247 mg (yield: 91.5%) of the title compound.

Workup

  1. temperatureAfter the reaction mixture was cooled
  2. extractionfollowed by extraction with ethyl acetate (20 ml×3)
  3. washThe organic layer was washed with 20 ml of water
  4. dry with materialdried over anhydrous sodium sulfate
  5. distillationthe solvent was distilled off
  6. customThe residue was purified by silica gel column chromatography (eluent: ethyl acetate-hexane=1/4)

Sources & evidence

ORD record
ord-850eebe6572746caa58be56132a15bf0
Source dataset
uspto-grants-2002_01
Patent number
US06339089B2

Reaction notes

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