Allylamine → HCID 18326399, compound

HRID 1250616Notes

Reaction equation

HRID 1250616 reaction equation
[CH2:1]([NH2:4])[CH:2]=[CH2:3].[CH2:5]([NH:8][C:9]1[C:10]2[S:18][CH:17]=[C:16]([CH3:19])[C:11]=2[N:12]=[C:13](Cl)[N:14]=1)[CH:6]=[CH2:7]>O>[CH2:1]([NH:4][C:13]1[N:14]=[C:9]([NH:8][CH2:5][CH:6]=[CH2:7])[C:10]2[S:18][CH:17]=[C:16]([CH3:19])[C:11]=2[N:12]=1)[CH:2]=[CH2:3]

Participants

4

Reactant 2

HCID 7853AllylamineHCID 18326500HCID 18326500, compound

Product 1

HCID 18326399HCID 18326399, compoundYield 85.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
140 °C

Procedure

In 2.28 g (40.0 mmol) of allylamine was suspended 250 mg (1.1 mmol) of 4-allylamino-2-chloro-7-methylthieno[3,2-d]pyrimidine, and the resulting mixture was heated in a sealed tube at 140° C. for 24 hours. After the reaction mixture was cooled, 50 ml of water was added thereto, followed by extraction with ethyl acetate (50 ml×3). The organic layer was washed with water and dried over anhydrous sodium sulfate, and then the solvent was distilled off. The residue was purified by silica gel chromatography (eluent: ethyl acetate-hexane=4/1) to give 233 mg (yield: 85.7%) of the title compound.

Workup

  1. temperatureAfter the reaction mixture was cooled
  2. extractionfollowed by extraction with ethyl acetate (50 ml×3)
  3. washThe organic layer was washed with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. distillationthe solvent was distilled off
  6. customThe residue was purified by silica gel chromatography (eluent: ethyl acetate-hexane=4/1)

Sources & evidence

ORD record
ord-493d1b7e2266463d9612b5064aabc32f
Source dataset
uspto-grants-2002_01
Patent number
US06339089B2

Reaction notes

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