Reaktion #215113

Reaktionsgleichung

potassium hydroxide

potassium iodide

2,4-diamino-5-(3'-hydroxy-4'-methoxybenzyl)pyrimidine hydrochloride

3-(p-acetamidophenylthio)propyl chloride

→

2,4-Diamino-5-{3'-[3"-(p-acetamidophenylthio)propoxy]-4-methoxybenzyl}pyrimidine

Lösungsmittel

methanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturis heated
2. 2
   Temperaturat reflux for 20 hr
3. 3
   TemperaturThe mixture is cooled
4. 4
   Filtrationfiltered
5. 5
   Sonstigeto remove a small amount of inorganic material
6. 6
   workup.ADDITIONWater, (75 ml) is added to the filtrate
7. 7
   Sonstigethe methanol is removed by vacuum distillation
8. 8
   workup.ADDITIONAfter the addition of 50 ml of methylene chloride the mixture
9. 9
   Filtrationfiltered
10. 10
    Sonstigeto obtain a crystalline product
11. 11
    SonstigeAfter twice recrystallizing from 50% aqueous ethanol the product 2,4-diamino-5-{3'-[3"-(p-acetamidophenylthio)propoxy]-4'-methoxybenzyl}pyrimidine, weighes 1.94 g

Vorschrift

A mixture of 3.6 g of 2,4-diamino-5-(3'-hydroxy-4'-methoxybenzyl)pyrimidine hydrochloride, 3.4 g of 3-(p-acetamidophenylthio)propyl chloride, 3.8 ml of methanol, 12 ml of an aqueous solution containing 0.027 mole of potassium hydroxide and 0.2 g of potassium iodide is heated at reflux for 20 hr. The mixture is cooled and filtered to remove a small amount of inorganic material. Water, (75 ml) is added to the filtrate, and the methanol is removed by vacuum distillation. After the addition of 50 ml of methylene chloride the mixture is stirred for 30 min. and then filtered to obtain a crystalline product. After twice recrystallizing from 50% aqueous ethanol the product 2,4-diamino-5-{3'-[3"-(p-acetamidophenylthio)propoxy]-4'-methoxybenzyl}pyrimidine, weighes 1.94 g and has m.p. 175°-177°.

Quelle