Allylamine → HCID 18326523, compound

HRID 1250668Notes

Reaction equation

HRID 1250668 reaction equation
Cl[C:2]1[N:3]=[C:4]([NH:12][CH2:13][C:14]([CH3:16])=[CH2:15])[C:5]2[S:10][CH:9]=[C:8]([CH3:11])[C:6]=2[N:7]=1.[CH2:17]([NH2:20])[CH:18]=[CH2:19].C(=O)([O-])O.[Na+]>>[CH2:17]([NH:20][C:2]1[N:3]=[C:4]([NH:12][CH2:13][C:14]([CH3:16])=[CH2:15])[C:5]2[S:10][CH:9]=[C:8]([CH3:11])[C:6]=2[N:7]=1)[CH:18]=[CH2:19]

Participants

4

Reactant 3

HCID 7853AllylamineHCID 516892Sodium BicarbonateHCID 18326396HCID 18326396, compound

Product 1

HCID 18326523HCID 18326523, compoundYield 32.8%

Procedure

305 mg (1.2 mmol) of 2-chloro-7-methyl-4-(2-methyl-2-propenylamino)thieno[3,2-d]pyrimidine and 1.14 g (19.2 mmol) of allylamine were heated in a sealed tube at 160° C. for 16 hours. After completion of the reaction, the reaction mixture was allowed to resume room temperature, followed by adding a saturated aqueous sodium hydrogen carbonate solution thereto and extraction with ethyl acetate (50 ml×2). After the organic layer was washed with brine and dried over anhydrous sodium sulfate, the solvent was distilled off. The residue was purified by silica gel chromatography (eluent: ethyl acetate-hexane=1/4) to give 108 mg (yield: 32.7%) of the title compound.

Workup

  1. customAfter completion of the reaction
  2. customto resume room temperature
  3. extractionextraction with ethyl acetate (50 ml×2)
  4. washAfter the organic layer was washed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. distillationthe solvent was distilled off
  7. customThe residue was purified by silica gel chromatography (eluent: ethyl acetate-hexane=1/4)

Sources & evidence

ORD record
ord-de781bd15e2a408384179f883ef7ae8f
Source dataset
uspto-grants-2002_01
Patent number
US06339089B2

Reaction notes

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