Diallylamine → HCID 18326450, compound

HRID 1250627Notes

Reaction equation

HRID 1250627 reaction equation
[CH2:1]([NH:4][C:5]1[C:6]2[S:14][CH:13]=[C:12]([CH3:15])[C:7]=2[N:8]=[C:9]([Cl:11])[N:10]=1)[CH:2]=[CH2:3].[CH2:16]([NH:19][CH2:20][CH:21]=[CH2:22])[CH:17]=[CH2:18].C(=O)([O-])O.[Na+]>>[ClH:11].[CH2:1]([NH:4][C:5]1[C:6]2[S:14][CH:13]=[C:12]([CH3:15])[C:7]=2[N:8]=[C:9]([N:19]([CH2:20][CH:21]=[CH2:22])[CH2:16][CH:17]=[CH2:18])[N:10]=1)[CH:2]=[CH2:3]

Participants

4

Reactant 3

HCID 31279DiallylamineHCID 516892Sodium BicarbonateHCID 18326500HCID 18326500, compound

Product 1

HCID 18326450HCID 18326450, compound

Procedure

In a sealed tube were heated 287 mg (1.2 mmol) of 4-allylamino-2-chloro-7-methylthieno[3,2-d]pyrimidine and 1.87 g (19.2 mmol) of diallylamine at 160° C. for 16 hours. After completion of the reaction, the reaction mixture was allowed to resume room temperature, and a saturated aqueous sodium hydrogen carbonate solution was added thereto, followed by extraction with ethyl acetate (50 ml×2). The organic layer was washed with brine and dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure. The residue was purified by silica gel chromatography (eluent: ethyl acetate-hexane=1/4) to give 193 mg (yield: 53.7%) of a free base compound of the title compound.

Workup

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

Sources & evidence

ORD record
ord-0b96c908efe147d6897db27479ffb4cc
Source dataset
uspto-grants-2002_01
Patent number
US06339089B2

Reaction notes

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