Ethylamine → 2-Amino-4-(2-methyl-5-propylaminomethyl-phenyl)-thieno[2,3-d]pyrimidine-6-carboxylic acid ethylamide

HRID 1161734

Reaktionsgleichung

Reaktionsgleichung von HRID 1161734
C([O:3][C:4]([C:6]1[S:24][C:9]2[N:10]=[C:11]([NH2:23])[N:12]=[C:13]([C:14]3[CH:19]=[C:18]([CH:20]=O)[CH:17]=[CH:16][C:15]=3[CH3:22])[C:8]=2[CH:7]=1)=O)C.[CH2:25]([NH2:28])[CH2:26][CH3:27].[BH4-].[Na+].[CH2:31]([NH2:33])[CH3:32]>CO>[CH2:31]([NH:33][C:4]([C:6]1[S:24][C:9]2[N:10]=[C:11]([NH2:23])[N:12]=[C:13]([C:14]3[CH:19]=[C:18]([CH2:20][NH:28][CH2:25][CH2:26][CH3:27])[CH:17]=[CH:16][C:15]=3[CH3:22])[C:8]=2[CH:7]=1)=[O:3])[CH3:32]

Komponenten

6

Edukt 4

HCID 6341EthylamineHCID 7852PropylamineHCID 4311764Sodium borohydrideHCID 595191892-Amino-4-(5-formyl-2-methyl-phenyl)-thieno[2,3-d]pyrimidine-6-carboxylic acid ethyl ester

Produkt 1

HCID 595191982-Amino-4-(2-methyl-5-propylaminomethyl-phenyl)-thieno[2,3-d]pyrimidine-6-carboxylic acid ethylamideAusbeute 45 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel2×

Versuchsvorschrift

Methanol (5 mL) was added to 2-Amino-4-(5-formyl-2-methyl-phenyl)-thieno[2,3-d]pyrimidine-6-carboxylic acid ethyl ester (100 mg, 0.29 mmol) and propylamine (0.586 mmol) then added to resulting suspension. Reaction mixture was heated to reflux (affording homogeneous brown solution) for 4 hours then allowed to cool to ambient temperature. Sodium borohydride (23 mg; 0.58 mmol) was added and reaction mixture stirred for 30 mins. Methanol was removed in vacuo and the residue was partitioned between water (20 mL) and ethyl acetate (20 mL). The phases were separated and organic phase was dried over Na2SO4 and filtered, and filtrate solvents removed in vacuo to afford brown solid which was suspended 2.0M ethylamine in methanol solution (5.0 mL, 10 mmol) and heated in sealed tube at 85 degrees C. overnight. Reaction mixture was allowed to cool and solvents removed in vacuo to afford a brown solid which was triturated in hot ethyl acetate, filtered and dried to afford title product as light-brown solid (50 mg, 45%)

Aufarbeitung

  1. additionthen added
  2. customto resulting suspension
  3. customReaction mixture
  4. temperaturewas heated
  5. temperatureto reflux
  6. custom(affording homogeneous brown solution) for 4 hours
  7. customreaction mixture
  8. customMethanol was removed in vacuo
  9. customthe residue was partitioned between water (20 mL) and ethyl acetate (20 mL)
  10. customThe phases were separated
  11. dry with materialorganic phase was dried over Na2SO4
  12. filtrationfiltered
  13. customfiltrate solvents removed in vacuo
  14. customto afford brown solid which
  15. temperatureheated in sealed tube at 85 degrees C
  16. customovernight
  17. customReaction mixture
  18. temperatureto cool
  19. customsolvents removed in vacuo
  20. customto afford a brown solid which
  21. customwas triturated in hot ethyl acetate
  22. filtrationfiltered
  23. customdried

Quellen und Nachweise

ORD-Eintrag
ord-774d7f51538d45e898f6e101f0d16c06
Quelldatensatz
uspto-grants-2010_10
Patentnummer
US07820658B2

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