Potassium Iodide → HCID 15571592, compound

HRID 127931Notes

Reaction equation

HRID 127931 reaction equation
Cl.[NH2:2][C:3]1[N:8]=[C:7]([NH2:9])[C:6]([CH2:10][C:11]2[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[C:13]([OH:19])[CH:12]=2)=[CH:5][N:4]=1.[C:20]([NH:23][C:24]1[CH:29]=[CH:28][C:27]([S:30][CH2:31][CH2:32][CH2:33]Cl)=[CH:26][CH:25]=1)(=[O:22])[CH3:21].[OH-].[K+].[I-].[K+]>CO>[NH2:2][C:3]1[N:8]=[C:7]([NH2:9])[C:6]([CH2:10][C:11]2[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[C:13]([O:19][CH2:33][CH2:32][CH2:31][S:30][C:27]3[CH:28]=[CH:29][C:24]([NH:23][C:20](=[O:22])[CH3:21])=[CH:25][CH:26]=3)[CH:12]=2)=[CH:5][N:4]=1

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 14797Potassium HydroxideHCID 14005891N-{4-[(3-Chloropropyl)sulfanyl]phenyl}acetamideHCID 15571588HCID 15571588, compound

Product 1

HCID 15571592HCID 15571592, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

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°.

Workup

  1. temperatureis heated
  2. temperatureat reflux for 20 hr
  3. temperatureThe mixture is cooled
  4. filtrationfiltered
  5. customto remove a small amount of inorganic material
  6. additionWater, (75 ml) is added to the filtrate
  7. customthe methanol is removed by vacuum distillation
  8. additionAfter the addition of 50 ml of methylene chloride the mixture
  9. filtrationfiltered
  10. customto obtain a crystalline product
  11. customAfter twice recrystallizing from 50% aqueous ethanol the product 2,4-diamino-5-{3'-[3"-(p-acetamidophenylthio)propoxy]-4'-methoxybenzyl}pyrimidine, weighes 1.94 g

Sources & evidence

ORD record
ord-11226529870a4c3da0f0599f67bedf74
Source dataset
uspto-grants-1981_03
Patent number
US04258045

Reaction notes

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