Dimethylformamide → 2-(2-Diisopropylaminoethylamino)-4,6-dimethylpyrimidine

HRID 614308노트

반응식

HRID 614308 반응식
CN(C)C=O.[C:6]([NH:9][C:10]1[N:15]=[C:14]([CH3:16])[CH:13]=[C:12]([CH3:17])[N:11]=1)(=O)[CH3:7].Cl.[CH:19]([N:22]([CH:26]([CH3:28])[CH3:27])CCCl)([CH3:21])[CH3:20].[H-].[Na+]>C(O)C>[CH:19]([N:22]([CH:26]([CH3:28])[CH3:27])[CH2:7][CH2:6][NH:9][C:10]1[N:15]=[C:14]([CH3:16])[CH:13]=[C:12]([CH3:17])[N:11]=1)([CH3:21])[CH3:20]

참가 물질

6

반응물 4

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 779422-Chloroethyldiisopropylammonium chlorideHCID 34892962-Acetamido-4,6-dimethylpyrimidine

생성물 1

HCID 233499002-(2-Diisopropylaminoethylamino)-4,6-dimethylpyrimidine

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

To 600 ml of dry dimethylformamide is added 2-acetamido-4,6-dimethylpyrimidine (34.8 g., 0.21 mole) and 2-diisopropylaminoethyl chloride hydrochloride (48 g., 0.24 mole). The mixture is stirred under nitrogen and sodium hydride (50% in mineral oil) (24.7 g., 0.515 mole) is added in portions over one hour while the temperature is maintained below 45° C. The mixture is then heated at 75°-78° C. for 1/2 hour and then at 90°-95° C. for 31/2 hours. On cooling, ethanol, 25 ml, is added and the solvents removed under reduced pressure. The residue is suspended in 75 ml of 1-propanol and 400 ml of 5N sodium hydroxide and refluxed with stirring for 18 hours. On cooling the mixture is extracted with methylene chloride. The organic extracts are then extracted with dilute hydrochloric acid. The acid extracts are extracted with hexane and then made alkaline with a molar excess of sodium hydroxide. The crude product is extracted from the basic solution with diethyl ether. The ethereal extracts are washed with saturated sodium chloride solution, dried over sodium sulfate and concentrated under vacuum. The residue is distilled and the product diamine (37.2 g., 0.149 mole) collected at 130°-134° C./0.4 mm; melting point 79.5°-82° C.

후처리

  1. temperatureis maintained below 45° C
  2. temperatureThe mixture is then heated at 75°-78° C. for 1/2 hour
  3. customat 90°-95° C.
  4. custom2 hours
  5. temperatureOn cooling
  6. customthe solvents removed under reduced pressure
  7. temperature400 ml of 5N sodium hydroxide and refluxed
  8. stirringwith stirring for 18 hours
  9. temperatureOn cooling the mixture
  10. extractionis extracted with methylene chloride
  11. extractionThe organic extracts are then extracted with dilute hydrochloric acid
  12. extractionThe acid extracts are extracted with hexane
  13. extractionThe crude product is extracted from the basic solution with diethyl ether
  14. washThe ethereal extracts are washed with saturated sodium chloride solution
  15. dry with materialdried over sodium sulfate
  16. concentrationconcentrated under vacuum
  17. distillationThe residue is distilled

출처 및 근거

ORD 기록
ord-98315c68af114fa08e799e3c656214e1
출처 데이터셋
uspto-grants-1979_03
특허 번호
US04144338

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