Allylamine → HCID 18326404, compound

HRID 1250649Notes

Reaction equation

HRID 1250649 reaction equation
Cl[C:2]1[N:3]=[C:4]([NH:12][CH:13]([CH3:16])[CH2:14][CH3:15])[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][CH:13]([CH3:16])[CH2:14][CH3:15])[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 18326459HCID 18326459, compound

Product 1

HCID 18326404HCID 18326404, compoundYield 80.2%

Procedure

In a sealed tube were heated 307 mg (1.2 mmol) of 2-chloro-7-methyl-4-(1-methylpropylamino)thieno[3,2-d]pyrimidine and 1.10 g (19.2 mmol) of allylamine 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=1/10) to give 266 mg (yield: 80.1%) 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=1/10)

Sources & evidence

ORD record
ord-c1f0c59de65343de8e2ee655f9cf1e38
Source dataset
uspto-grants-2002_01
Patent number
US06339089B2

Reaction notes

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