Acetic Acid → HCID 178517559, Verbindung

HRID 2036775Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2036775
CO[C:3]([C:5]1[CH:6]=[N:7][CH:8]=[N:9][CH:10]=1)=[NH:4].[NH2:11][C:12]1[CH:20]=[CH:19][CH:18]=[C:17]([Br:21])[C:13]=1[C:14]([OH:16])=O.C(O)(=O)C>CO>[Br:21][C:17]1[CH:18]=[CH:19][CH:20]=[C:12]2[C:13]=1[C:14]([OH:16])=[N:4][C:3]([C:5]1[CH:6]=[N:7][CH:8]=[N:9][CH:10]=1)=[N:11]2

Komponenten

5

Edukt 3

HCID 176Acetic AcidHCID 105606492-Amino-6-bromobenzoic acidHCID 45080301Methyl pyrimidine-5-carboximidate

Produkt 1

HCID 178517559HCID 178517559, VerbindungAusbeute 27,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel2×

Versuchsvorschrift

To a stirred suspension of methylpyrimidine-5-carbimidate (2.00 g, 14.5 mmol) in methanol (20 mL) was added 2-amino-6-bromobenzoic acid (3.1 g, 14.5 mmol). The mixture was heated to reflux where it stirred for 16 h under the nitrogen atmosphere. At the conclusion of this period, acetic acid (2.72 ml, 47 mmol) was added drop wise. Upon completion of addition, methanol was evaporated under reduced pressure to yield a residue. The residue was triturated with ether (100 mL), ethyl acetate (50 mL) and the resulting solid was dried to yield 5-bromo-2-(pyrimidin-5-yl)quinazolin-4-ol (1.2 g, 27%) as an off-white solid. The crude product was used without further purification. 1H NMR (400 MHz, DMSO-d6, δ): 7.64 (dd, J=7.2 Hz, 8.4 Hz, 1H); 7.73-7.75 (m, 2H); 9.35 (s, 1H); 9.46 (s, 2H); 12.9 (br s, 1H). ES-MS: [M++1]=303 and [M++3]=305.

Aufarbeitung

  1. temperatureThe mixture was heated
  2. temperatureto reflux where it
  3. customwas evaporated under reduced pressure
  4. customto yield a residue
  5. customThe residue was triturated with ether (100 mL), ethyl acetate (50 mL)
  6. customthe resulting solid was dried

Quellen und Nachweise

ORD-Eintrag
ord-980bd968c0aa41a7881428819a4535c2
Quelldatensatz
uspto-grants-2013_11
Patentnummer
US08575184B2

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