Lithium hydroxide, monohydrate → 2,4-Diamino-6-ethyl-5-(3-(2-(3-carboxypropoxy)phenoxy)propoxy)pyrimidine

HRID 40815Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 40815
[NH2:1][C:2]1[N:7]=[C:6]([NH2:8])[C:5]([OH:9])=[C:4]([CH2:10][CH3:11])[N:3]=1.O.[OH-].[Li+].Br[CH2:16][CH2:17][CH2:18][O:19][C:20]1[CH:34]=[CH:33][CH:32]=[CH:31][C:21]=1[O:22][CH2:23][CH2:24][CH2:25][C:26]([O:28]CC)=[O:27]>CN(C=O)C.O>[NH2:1][C:2]1[N:7]=[C:6]([NH2:8])[C:5]([O:9][CH2:16][CH2:17][CH2:18][O:19][C:20]2[CH:34]=[CH:33][CH:32]=[CH:31][C:21]=2[O:22][CH2:23][CH2:24][CH2:25][C:26]([OH:28])=[O:27])=[C:4]([CH2:10][CH3:11])[N:3]=1

Komponenten

6

Edukt 3

HCID 168937Lithium hydroxide, monohydrateHCID 205093882,4-Diamino-6-ethylpyrimidin-5-olHCID 68574422Ethyl 4-(2-(3-bromopropoxy)phenoxy)butanoate

Produkt 1

HCID 252605752,4-Diamino-6-ethyl-5-(3-(2-(3-carboxypropoxy)phenoxy)propoxy)pyrimidineAusbeute 59 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel2×

Reaktionsbedingungen

Temperatur
25 °C

Versuchsvorschrift

2,4-Diamino-6-ethyl-5-hydroxypyrimidine (0.4625 g, 3 mmol) was added to a stirred solution of lithium hydroxide monohydrate (0.4406 g, 10.5 mmol) in DMF (4 mL) and the reaction mixture was stirred at 25° C. for 1 hour. A solution of ethyl 4-(2-(3-bromopropoxy)phenoxy)butanoate (1.0357 g, 3 mmol) in DMF (1 mL) was added and the reaction mixture was left stirring at 25° C. overnight. DMF was partially removed under reduced pressure to give residue. The residue was diluted with water and extracted with dichloromethane. The aqueous layer was neutralized with dilute HCl to give white solid. Recrystallization with acetone afforded the desired diaminopyrimidine as white solid (0.6911 g, 59%, m.p. 204-206° C.). 1H NMR (400 MHz, DMSO-d6): 1.10 (3H, t, J=7.5 Hz), 1.91 (2H, m), 2.14 (2H, m), 2.31-2.39 (4H, m), 3.78 (2H, t, J=6.1 Hz), 3.96 (2H, t, J=6.4 Hz), 4.13 (2H, t, J=6.1 Hz), 5.60 (2H, s), 6.09 (2H, s), 6.86-6.90 (2H, m), 6.95-7.01 (2H, m).

Aufarbeitung

  1. waitthe reaction mixture was left
  2. stirringstirring at 25° C. overnight
  3. customDMF was partially removed under reduced pressure
  4. customto give residue
  5. extractionextracted with dichloromethane
  6. customto give white solid
  7. customRecrystallization with acetone

Quellen und Nachweise

ORD-Eintrag
ord-117d26b66f6740e998de4feed01a4394
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08530491B2

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