Isopropanol → HCID 67382070, Verbindung

HRID 910199Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 910199
Cl[C:2]1[C:3]2[C:12]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)=[CH:11][S:10][C:4]=2[N:5]=[C:6]([CH2:8][Cl:9])[N:7]=1.[NH2:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][N:22]=1.C(N(CC)CC)C.CC(O)C>O>[Cl:9][CH2:8][C:6]1[N:7]=[C:2]([NH:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][N:22]=2)[C:3]2[C:12]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)=[CH:11][S:10][C:4]=2[N:5]=1

Komponenten

6

Edukt 4

HCID 3776IsopropanolHCID 8471TriethylamineHCID 195092-PyridinemethanamineHCID 23726818HCID 23726818, Verbindung

Produkt 1

HCID 67382070HCID 67382070, VerbindungAusbeute 27,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

A reaction mixture of 4-chloro-2-chloromethyl-5-phenylthieno[2,3-d]pyrimidine (0.50 g, 1.69 mmol), 2-aminomethylpyridine (0.17 ml, 1.69 mmol), triethylamine (0.26 ml, 1.86 mmol) and propan-2-ol (15 ml) was stirred at ambient temperature for 4 days. The solution was then poured into water (150 ml) and extracted with ethyl acetate (3×75 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 (1:4) gave (2-chloromethyl-5-phenylthieno[2,3-d]pyrimidin-4-yl)pyridin-2-ylmethylamine as a yellow solid (0.17 g), m.p. 97°-99° C.

Aufarbeitung

  1. extractionextracted with ethyl acetate (3×75 ml)
  2. dry with materialThe combined organic extracts were dried (MgSO4)
  3. customthe solvent removed in vacuo
  4. customto give the crude product
  5. customPurification by flash chromatography (silica)
  6. washeluting with ethyl acetate and 40°-60° petroleum ether (1:4)

Quellen und Nachweise

ORD-Eintrag
ord-1f6571ee506d45bc920636b66ce7ac56
Quelldatensatz
uspto-grants-2011_09
Patentnummer
US08022076B2

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