Allylamine → HCID 15908139, compound

Reaction equation

[C:1]([NH:5][C:6]1[C:7]2[S:15][CH:14]=[C:13]([CH2:16][CH2:17][CH3:18])[C:8]=2[N:9]=[C:10](Cl)[N:11]=1)([CH3:4])([CH3:3])[CH3:2].[CH2:19]([NH2:22])[CH:20]=[CH2:21].C(=O)([O-])O.[Na+]>>[CH2:19]([NH:22][C:10]1[N:11]=[C:6]([NH:5][C:1]([CH3:4])([CH3:3])[CH3:2])[C:7]2[S:15][CH:14]=[C:13]([CH2:16][CH2:17][CH3:18])[C:8]=2[N:9]=1)[CH:20]=[CH2:21]

Participants

Reactant 3

HCID 7853Allylamine

HCID 516892Sodium Bicarbonate

HCID 15908138HCID 15908138, compound

Product 1

HCID 15908139HCID 15908139, compoundYield 76.5%

Procedure

173 mg (0.61 mmol) of 4-t-butylamino-2-chloro-7-propylthieno[3,2-d]pyrimidine and 557 mg (9.8 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 142 mg (yield: 76.3%) of the title compound.