1-Propanol → 4-(5-Bromo-2-propoxy-phenyl)-6-chloro-pyrimidin-2-ylamine

HRID 28629

Reaktionsgleichung

Reaktionsgleichung von HRID 28629
[NH2:1][C:2]1[N:7]=[C:6]([C:8]2[CH:13]=[C:12]([Br:14])[CH:11]=[CH:10][C:9]=2[OH:15])[CH:5]=[C:4]([Cl:16])[N:3]=1.[CH2:17](O)[CH2:18][CH3:19].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>O1CCCC1>[Br:14][C:12]1[CH:11]=[CH:10][C:9]([O:15][CH2:17][CH2:18][CH3:19])=[C:8]([C:6]2[CH:5]=[C:4]([Cl:16])[N:3]=[C:2]([NH2:1])[N:7]=2)[CH:13]=1

Komponenten

6

Edukt 4

HCID 10311-PropanolHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 1360800122-(2-Amino-6-chloro-pyrimidin-4-yl)-4-bromo-phenol

Produkt 1

HCID 860043744-(5-Bromo-2-propoxy-phenyl)-6-chloro-pyrimidin-2-ylamineAusbeute 52,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To the stirred solution of 2-(2-amino-6-chloro-pyrimidin-4-yl)-4-bromo-phenol (0.060 g, 0.20 mmol), 1-propanol (0.036 g, 0.60 mmol), and triphenylphosphine (0.157 g, 0.60 mmol) in tetrahydrofuran (5.0 ml) was added diethyl azodicarboxylate (0.104 g, 0.60 mmol). After stirring for 16 hours, the mixture was concentrated under reduced pressure. The residue was purified by flash chromatography on silica gel eluting with ethyl acetate-hexane (1:6) to provide 4-(5-bromo-2-propoxy-phenyl)-6-chloro-pyrimidin-2-ylamine (0.036 g, 52% yield) as a white powder.

Aufarbeitung

  1. concentrationthe mixture was concentrated under reduced pressure
  2. customThe residue was purified by flash chromatography on silica gel eluting with ethyl acetate-hexane (1:6)

Quellen und Nachweise

ORD-Eintrag
ord-83dda32384ec47fbba0a02bb6e16db17
Quelldatensatz
uspto-grants-2008_09
Patentnummer
US07419984B2

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