Allylamine → HCID 18326563, compound

HRID 1250655Notes

Reaction equation

HRID 1250655 reaction equation
Cl[C:2]1[N:3]=[C:4]([NH:12][N:13]([CH3:15])[CH3:14])[C:5]2[S:10][CH:9]=[C:8]([CH3:11])[C:6]=2[N:7]=1.[CH2:16]([NH2:19])[CH:17]=[CH2:18].C(=O)([O-])O.[Na+]>>[CH2:16]([NH:19][C:2]1[N:3]=[C:4]([NH:12][N:13]([CH3:15])[CH3:14])[C:5]2[S:10][CH:9]=[C:8]([CH3:11])[C:6]=2[N:7]=1)[CH:17]=[CH2:18]

Participants

4

Reactant 3

HCID 7853AllylamineHCID 516892Sodium BicarbonateHCID 18326492HCID 18326492, compound

Product 1

HCID 18326563HCID 18326563, compoundYield 92.6%

Procedure

150 mg (0.62 mmol) of 2-chloro-7-methyl-4-(2,2-dimethylhydrazino)thieno[3,2-d]pyrimidine and 564 mg (9.89 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 a silica gel chromatography (eluent: ethyl acetate-hexane=1/2) to give 151 mg (yield: 92.6%) 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 a silica gel chromatography (eluent: ethyl acetate-hexane=1/2)

Sources & evidence

ORD record
ord-5dd6ea14b4f74cbd98c1d01cf335a711
Source dataset
uspto-grants-2002_01
Patent number
US06339089B2

Reaction notes

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