Boron tribromide → HCID 68669560, Verbindung

HRID 2071048Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2071048
[CH:1]([C:4]1[CH:9]=[C:8]([CH2:10][O:11]C)[N:7]=[C:6]([NH2:13])[N:5]=1)([CH3:3])[CH3:2].B(Br)(Br)Br>C(Cl)Cl>[NH2:13][C:6]1[N:7]=[C:8]([CH2:10][OH:11])[CH:9]=[C:4]([CH:1]([CH3:3])[CH3:2])[N:5]=1

Komponenten

4

Edukt 2

HCID 25134Boron tribromideHCID 68671207HCID 68671207, Verbindung

Produkt 1

HCID 68669560HCID 68669560, VerbindungAusbeute 66 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a stirred solution of 4-isopropyl-6-(methoxymethyl)pyrimidin-2-amine (537 mg, 3.0 mmol) in CH2Cl2 (30 mL) at 0° C. was added BBr3 (3 mL of 1.0 M solution, 3 mmol) dropwise. The reaction was quenched with saturated aqueous NaHCO3 after 4 h. The resulting mixture was extracted with CH2Cl2 (2×20 mL). The combined organic layer was washed with brine, dried with Na2SO4 and concentrated under reduced pressure to provide (2-amino-6-isopropylpyrimidin-4-yl)methanol as a dark brown oil which was used for next step without further purification. 1H NMR (CDCl3): d 6.49 (s, 1H), 5.06 (br, 2H), 4.59 (s, 2H), 2.78-2.87 (m, 1H), 1.25 (m, 6H).

Aufarbeitung

  1. customThe reaction was quenched with saturated aqueous NaHCO3 after 4 h
  2. extractionThe resulting mixture was extracted with CH2Cl2 (2×20 mL)
  3. washThe combined organic layer was washed with brine
  4. dry with materialdried with Na2SO4
  5. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-fa150b091b634ab7b6191ff45a850fd0
Quelldatensatz
uspto-grants-2012_10
Patentnummer
US08299267B2

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