Ethanol → (5-Bromothieno[2,3-d]pyrimidin-4-yl)pyridin-2-ylmethylamine

HRID 910202

Reaktionsgleichung

Reaktionsgleichung von HRID 910202
[Br:1][C:2]1[C:10]2[C:9](Cl)=[N:8][CH:7]=[N:6][C:5]=2[S:4][CH:3]=1.C(O)C.C(N(CC)CC)C.[NH2:22][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][N:25]=1>O>[Br:1][C:2]1[C:10]2[C:9]([NH:22][CH2:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][N:25]=3)=[N:8][CH:7]=[N:6][C:5]=2[S:4][CH:3]=1

Komponenten

6

Edukt 4

HCID 702EthanolHCID 8471TriethylamineHCID 195092-PyridinemethanamineHCID 454802995-Bromo-4-chlorothieno[2,3-d]pyrimidine

Produkt 1

HCID 67381984(5-Bromothieno[2,3-d]pyrimidin-4-yl)pyridin-2-ylmethylamineAusbeute 63,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

A stirred mixture of 5-bromo-4-chlorothieno[2,3-d]pyrimidine (3.8 g, 15.2 mmol), ethanol (250 ml), triethylamine (2.32 ml, 16.7 mmol) and 2-aminomethylpyridine (1.72 ml, 16.7 mmol) was heated under reflux for 2.5 hours. The solution was then cooled to ambient temperature, poured into water (300 ml) and extracted with dichloromethane (3×150 ml). The combined organic extracts were dried (MgSO4) and the solvent removed in vacuo to give the crude product. Purification by flash chromatography (silica) eluting with ethyl acetate and 40°-60° petroleum ether (1:1) gave (5-bromothieno[2,3-d]pyrimidin-4-yl)pyridin-2-ylmethylamine as a yellow solid (3.12 g), m.pt. 127°-129° C.

Aufarbeitung

  1. temperaturewas heated
  2. temperatureunder reflux for 2.5 hours
  3. extractionextracted with dichloromethane (3×150 ml)
  4. dry with materialThe combined organic extracts were dried (MgSO4)
  5. customthe solvent removed in vacuo
  6. customto give the crude product
  7. customPurification by flash chromatography (silica)
  8. washeluting with ethyl acetate and 40°-60° petroleum ether (1:1)

Quellen und Nachweise

ORD-Eintrag
ord-71d2c6e6e7b84271b2054899a74236be
Quelldatensatz
uspto-grants-2011_09
Patentnummer
US08022076B2

Verknüpfte Notizen

Wird geladen…