5-methoxy-2,3-dihydro-1H-pyrrole

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: According to Khim. Geterosikl. Soedin, 6, 765, 1975, ethyl-2-amino-4,5-dimethyl-thiophene-3-carboxylate is reacted with 2-methoxy-pyrroline in the presence of phosphoryl chloride and the obtained 2,3-dimethyl-4-oxo-5,6-tetramethylene-4H-thieno[2,3-d]pyrimidine is desulphurated in an alcoholic solution with Raney-nickel and thus 3-(1-methyl-propyl)-4-oxo-4,6,7,8-tetrahydro-pyrrolo[1,2-a]pyrimidine is obtained. In the complicated two-step synthesis the pyrrolo-pyrimidine derivative is obtained with a yield of 36.5%.

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Stir 32.7 g of 2-methoxypyrroline, 63.8 g of 4-phenylbenzylcyanide and 5 g of 1,5-diazabicyclo[5,4,0]undec-5-ene for 26 hours at 110°. After cooling, take up the mixture with 500 ml of diethyl ether. Filter the formed precipitate and recrystallize it from 400 ml of ethanol with activated charcoal to obtain 12.2 g (14% of theory) of the title compound (m.p. 168° to 170°). After cooling Filter the formed precipitate recrystallize it from 400 ml of ethanol with activated charcoal

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 4.2 g. of 2-methoxypyrroline are dissolved in 25 ml. of benzene and treated at room temperature with 6.6 g. of p-methoxybenzoyl chloride dissolved in 30 ml. of benzene. The mixture is stirred at room temperature for 60 minutes and at reflux for 4 hours. 30 ml. of benzene are then added and the mixture is boiled at reflux for a further 24 hours. The volatile constituents are distilled off, the residue is taken up in ethanol, the mixture is concentrated, the residue is triturated with diethyl ether, filtered and the filter cake is taken up in ethyl acetate. The ethyl acetate solution is washed with sodium bicarbonate solution and water, dried over sodium sulfate and concentrated. The residue is sublimed in vacuo and there is obtained 1-(p-methoxybenzoyl)-2-pyrrolidinone having a melting point of 119°-120° C. at reflux for 4 hours at reflux for a further 24 hours The volatile constituents are distilled off the mixture is concentrated the residue is triturated with diethyl ether filtered The ethyl acetate solution is washed with sodium bicarbonate solution and water dried over sodium sulfate concentrated

Conditions: temp:25.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 276 mg. of lithium hydride (98%), 40 ml. of benzene and 4.2 g. of 2-methoxypyrroline are boiled at reflux for 2 hours under nitrogen and while stirring well. After cooling to 25° C., 6.6 g. of p-methoxybenzoyl chloride dissolved in 25 ml. of benzene are added and the resulting mixture is stirred under reflux for 2 hours and at room temperature for 16 hours. 100 ml. of ethyl acetate followed by 3.0 g. of lithium hydroxide (98%) dissolved in 25 ml. of water are added to the mixture at room temperature within 15 minutes. The organic phase is washed neutral with water, dried over sodium sulfate and evaporated under reduced pressure. After recrystallization from ethanol, there is obtained 1-(p-methoxybenzoyl)-2-pyrrolidinone having a melting point of 119°-120° C. at reflux for 2 hours under nitrogen the resulting mixture is stirred under reflux for 2 hours and at room temperature for 16 hours The organic phase is washed neutral with water dried over sodium sulfate evaporated under reduced pressure After recrystallization from ethanol

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: According to Khim. Geterosikl. Soedin. 6, 765, 1975 ethyl-2-amino-4,5-dimethyl-thiophene-3-carboxylate is reacted with 2-methoxy-pyrroline in the presence of phosphoryl chloride and the obtained 2,3-dimethyl-4-oxo-5,6-tetramethylene-4H thieno[2,3-d]pyrimidine is desulphurated in an alcoholic solution wih Raney-nickel and thus 3-(1-methyl-propyl)-4-oxo-4,6,7,8-tetrahydropyrrolo[1,2-a]pyrimidine is obtained. In the complicated two-step synthesis the pyrrolo-pyrimidine derivative is obtained with a yield of 36.5%.

Conditions: temp:0.00; pressure:0.00; stir: