Triethylamine → (R)-2,6-dichloro-5-methyl-N-(tetrahydrofuran-3-yl)pyrimidin-4-amine

HRID 527463Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 527463
[Cl:1][C:2]1[N:7]=[C:6]([Cl:8])[C:5]([CH3:9])=[C:4](Cl)[N:3]=1.Cl.[O:12]1[CH2:16][CH2:15][C@@H:14]([NH2:17])[CH2:13]1.CCN(CC)CC>CCO>[Cl:1][C:2]1[N:3]=[C:4]([NH:17][C@@H:14]2[CH2:15][CH2:16][O:12][CH2:13]2)[C:5]([CH3:9])=[C:6]([Cl:8])[N:7]=1

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 2327892,4,6-Trichloro-5-methylpyrimidineHCID 46856371(3R)-3-Aminotetrahydrofuran hydrochloride

Produkt 1

HCID 90426233(R)-2,6-dichloro-5-methyl-N-(tetrahydrofuran-3-yl)pyrimidin-4-amineAusbeute 54,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A mixture of 2,4,6-trichloro-5-methylpyrimidine (2 g, 10.2 mmol), (R)-tetrahydrofuran-3-amine hydrochloride (1.12 g, 9.2 mmol) and Et3N (2.1 g, 20.3 mmol) in EtOH (20 mL) was stirred at room temperature for 14 h., concentrated under vacuum and the residue was purified by chromatographic column on silica gel (EtOAc/petroleum ether, gradient elution, from 1/0 to 2/1) to give the (R)-2,6-dichloro-5-methyl-N-(tetrahydrofuran-3-yl)pyrimidin-4-amine (1.25 g, 53% yield) as a white solid. ESI-LCMS (m/z): 248.1 [M+1]+.

Aufarbeitung

  1. concentrationconcentrated under vacuum
  2. customthe residue was purified by chromatographic column on silica gel (EtOAc/petroleum ether, gradient elution, from 1/0 to 2/1)

Quellen und Nachweise

ORD-Eintrag
ord-772f106915e948ccb144b2c781f961a0
Quelldatensatz
uspto-grants-2016_05
Patentnummer
US09346802B2

Notizen zur Reaktion

Wird geladen…