Allylamine → HCID 15908141, compound

Reaction equation

Cl[C:2]1[N:3]=[C:4]([NH:14][CH3:15])[C:5]2[S:10][CH:9]=[C:8]([CH2:11][CH2:12][CH3:13])[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:14][CH3:15])[C:5]2[S:10][CH:9]=[C:8]([CH2:11][CH2:12][CH3:13])[C:6]=2[N:7]=1)[CH:17]=[CH2:18]

Participants

Reactant 3

HCID 7853Allylamine

HCID 516892Sodium Bicarbonate

HCID 15908140HCID 15908140, compound

Product 1

HCID 15908141HCID 15908141, compoundYield 68.5%

Procedure

50 mg (0.21 mmol) of 2-chloro-4-methylamino-7-propylthieno[3,2-d]pyrimidine and 189 mg (3.31 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 37 mg (yield: 68.5%) of the title compound.