Citric Acid → Ethanesulfonic acid {6-[2-(5-bromo-pyrimidin-2-yloxy)-ethoxy]-5-p-tolyl-pyrimidin-4-yl}-amide

HRID 2252722

Reaktionsgleichung

Reaktionsgleichung von HRID 2252722
[OH:1][CH2:2][CH2:3][O:4][C:5]1[N:10]=[CH:9][N:8]=[C:7]([NH:11][S:12]([CH2:15][CH3:16])(=[O:14])=[O:13])[C:6]=1[C:17]1[CH:22]=[CH:21][C:20]([CH3:23])=[CH:19][CH:18]=1.[H-].[Na+].Cl[C:27]1[N:32]=[CH:31][C:30]([Br:33])=[CH:29][N:28]=1.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>C1COCC1>[Br:33][C:30]1[CH:29]=[N:28][C:27]([O:1][CH2:2][CH2:3][O:4][C:5]2[N:10]=[CH:9][N:8]=[C:7]([NH:11][S:12]([CH2:15][CH3:16])(=[O:13])=[O:14])[C:6]=2[C:17]2[CH:18]=[CH:19][C:20]([CH3:23])=[CH:21][CH:22]=2)=[N:32][CH:31]=1

Komponenten

6

Edukt 4

HCID 311Citric AcidHCID 24758Sodium hydrideHCID 6066655-Bromo-2-chloropyrimidineHCID 59645277Ethanesulfonic acid [6-(2-hydroxy-ethoxy)-5-p-tolyl-pyrimidin-4-yl]-amide

Produkt 1

HCID 10311226Ethanesulfonic acid {6-[2-(5-bromo-pyrimidin-2-yloxy)-ethoxy]-5-p-tolyl-pyrimidin-4-yl}-amideAusbeute 34,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

Ethanesulfonic acid [6-(2-hydroxy-ethoxy)-5-p-tolyl-pyrimidin-4-yl]-amide (135 mg) was dissolved in THF (15 ml) and sodium hydride (80 mg) was added followed by stirring for 15 min at 50° C. Then 2-chloro-5-bromo-pyrimidine (162 mg) was added and stirring was continued for 8 h at 70 C. The reaction mixture was poured onto ice water, acidified with solid citric acid and extracted with ethylacetate. The combined organic extracts were dried over magnesium sulfate and the solvent was evaporated. The crude material was purified by plate chromatography with ethyl acetate/hexane=½ to give ethanesulfonic acid {6-[2-(5-bromo-pyrimidin-2-yloxy)-ethoxy]-5-p-tolyl-pyrimidin-4-yl}-amide (68 mg) as a white powder. LC-MS: tR: 4.64, [M+H]+: 496.19.

Aufarbeitung

  1. stirringstirring
  2. waitwas continued for 8 h at 70 C
  3. additionThe reaction mixture was poured onto ice water
  4. extractionextracted with ethylacetate
  5. dry with materialThe combined organic extracts were dried over magnesium sulfate
  6. customthe solvent was evaporated
  7. customThe crude material was purified by plate chromatography with ethyl acetate/hexane=½

Quellen und Nachweise

ORD-Eintrag
ord-655d6fd4792649d384053cec1d355535
Quelldatensatz
uspto-grants-2008_01
Patentnummer
US07323465B2

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