Water → N-benzyl-6-chloropyrimidin-4-amine

HRID 58162Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 58162
Cl[C:2]1[CH:7]=[C:6]([Cl:8])[N:5]=[CH:4][N:3]=1.CCN(C(C)C)C(C)C.[CH2:18]([NH2:25])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.O>CC(O)C>[CH2:18]([NH:25][C:2]1[CH:7]=[C:6]([Cl:8])[N:5]=[CH:4][N:3]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Komponenten

6

Edukt 4

HCID 962WaterHCID 7504BenzylamineHCID 709434,6-DichloropyrimidineHCID 81531Diisopropylethylamine

Produkt 1

HCID 3771857N-benzyl-6-chloropyrimidin-4-amineAusbeute 68,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3776IsopropanolLösungsmittel

Versuchsvorschrift

To a solution of 4,6-dichloro-pyrimidine (1.5 g, 10 mmol) in iPrOH (40 mL) and DIPEA (1.55 g, 12 mmol) was added a solution of benzylamine (1.28 g, 12 mmol) at room temperature. The resulting mixture was stirred at room temperature for 2.5 hours. Water was added and the mixture was extracted with DCM. The combined extracts were washed with brine, dried over anhydrous Na2SO4, and concentrated to give the crude product, which was purified by flash chromatography on silica to obtain the title compound (1.5 g, yield: 68%) as a white solid. H NMR (300 MHz, CDCl3) δ 8.35 (br s, 1H), 7.20-7.38 (m, 5H), 6.35 (s, 1H), 4.52 (s, 2H); MS (ESI): 220 [M+H]+.

Aufarbeitung

  1. extractionthe mixture was extracted with DCM
  2. washThe combined extracts were washed with brine
  3. dry with materialdried over anhydrous Na2SO4
  4. concentrationconcentrated
  5. customto give the crude product, which
  6. customwas purified by flash chromatography on silica

Quellen und Nachweise

ORD-Eintrag
ord-bd7eb2ddea574471a3c85b558ca28f0c
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09434697B2

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