Allylamine → 2-Allylamino-4-dodecylamino-7-methylthieno[3,2-d]pyrimidine

Reaction equation

Cl[C:2]1[N:3]=[C:4]([NH:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])[C:5]2[S:10][CH:9]=[C:8]([CH3:11])[C:6]=2[N:7]=1.[CH2:25]([NH2:28])[CH:26]=[CH2:27].C(=O)([O-])O.[Na+]>>[CH2:25]([NH:28][C:2]1[N:3]=[C:4]([NH:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])[C:5]2[S:10][CH:9]=[C:8]([CH3:11])[C:6]=2[N:7]=1)[CH:26]=[CH2:27]

Participants

Reactant 3

HCID 7853Allylamine

HCID 516892Sodium Bicarbonate

HCID 183263802-Chloro-4-dodecylamino-7-methylthieno[3,2-d]pyrimidine

Product 1

HCID 183265552-Allylamino-4-dodecylamino-7-methylthieno[3,2-d]pyrimidineYield 44.8%

Procedure

442 mg (1.2 mmol) of 2-chloro-4-dodecylamino-7-methylthieno[3,2-d]pyrimidine and 1.10 g (19.2 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 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 209 mg (yield: 44.8%) of the title compound.