Ethanol → Diethyl 2-(4-benzylpiperazino)-4,5-pyrimidinedicarboxylate

反応式

[Na].S(O)(O)(=O)=O.[C:7]([N:10]1[CH2:15][CH2:14][N:13]([CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH2:12][CH2:11]1)(=[NH:9])[NH2:8].C(O[CH:26]=[C:27]([C:33]([C:35]([OH:37])=[O:36])=O)[C:28]([O:30][CH2:31][CH3:32])=[O:29])C.[CH2:38](O)[CH3:39]>>[CH2:16]([N:13]1[CH2:14][CH2:15][N:10]([C:7]2[N:8]=[C:33]([C:35]([O:37][CH2:38][CH3:39])=[O:36])[C:27]([C:28]([O:30][CH2:31][CH3:32])=[O:29])=[CH:26][N:9]=2)[CH2:11][CH2:12]1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

参加物

反応物 4

HCID 702Ethanol

HCID 27566524-Benzylpiperazine-1-carboxamidine hemisulfate

HCID 5360545Sodium

HCID 54255144Ethoxymethylene oxalacetic acid ethyl ester

生成物 1

HCID 13769871Diethyl 2-(4-benzylpiperazino)-4,5-pyrimidinedicarboxylate収率 96%

実験手順

To absolute ethanol with 0.91 g of sodium dissolved therein, 11.5 g of 1-amidino-4-benzylpiperazine sulfate was added. The resultant mixture was stirred at room temperature for 30 minutes, to which 8.8 g of ethyl ethoxymethyleneoxaloacetate [synthesized by the process described in J. Am. Chem. Soc., 73, 3684 (1951)] was added. After allowing them to react at room temperature for 2 days, the reaction was caused to proceed further for 1 hour while heating the reaction mixture under reflux. After cooling the reaction mixture to room temperature, ethanol was distilled off under reduced pressure and the residue was dissolved in a mixture of water and ethyl acetate. After separation of the water layer, the ethyl acetate layer was washed with water and then with saturated saline. After drying the ethyl acetate layer with magnesium sulfate, ethyl acetate was distilled off under reduced pressure to obtain 13.7 g of the above-identified compound as light brown crystals (yield: 96%).