Allylamine → HCID 18326569, compound

HRID 1250674Notes

Reaction equation

HRID 1250674 reaction equation
[CH2:1]([NH:4][C:5]1[C:6]2[S:14][CH:13]=[C:12]([CH2:15][CH3:16])[C:7]=2[N:8]=[C:9](Cl)[N:10]=1)[CH:2]=[CH2:3].[CH2:17]([NH2:20])[CH:18]=[CH2:19].C(=O)([O-])O.[Na+]>>[CH2:17]([NH:20][C:9]1[N:10]=[C:5]([NH:4][CH2:1][CH:2]=[CH2:3])[C:6]2[S:14][CH:13]=[C:12]([CH2:15][CH3:16])[C:7]=2[N:8]=1)[CH:18]=[CH2:19]

Participants

4

Reactant 3

HCID 7853AllylamineHCID 516892Sodium BicarbonateHCID 18326530HCID 18326530, compound

Product 1

HCID 18326569HCID 18326569, compoundYield 86.3%

Procedure

304 mg (1.2 mmol) of 4-allylamino-2-chloro-7-ethylthieno[3,2-d]pyrimidine and 1.10 g (19.2 mmol) of allylamine were heated in a sealed tube at 140° 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 284 mg (yield: 86.3%) 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-860e5ef61dc64cb091bc93659d176d58
Source dataset
uspto-grants-2002_01
Patent number
US06339089B2

Reaction notes

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