4,6-Dichloropyrimidine → 6-chloro-N-(2-(2-methoxyphenyl)propyl)pyrimidin-4-amine

HRID 2207708Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2207708
Cl[C:2]1[CH:7]=[C:6]([Cl:8])[N:5]=[CH:4][N:3]=1.[CH3:9][O:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[CH:17]([CH3:20])[CH2:18][NH2:19].CCN(C(C)C)C(C)C>C(O)(C)C>[Cl:8][C:6]1[N:5]=[CH:4][N:3]=[C:2]([NH:19][CH2:18][CH:17]([C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[O:10][CH3:9])[CH3:20])[CH:7]=1

Komponenten

5

Edukt 3

HCID 709434,6-DichloropyrimidineHCID 81531DiisopropylethylamineHCID 4080602-(2-Methoxyphenyl)propan-1-amine

Produkt 1

HCID 866996526-chloro-N-(2-(2-methoxyphenyl)propyl)pyrimidin-4-amineAusbeute 77 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3776IsopropanolLösungsmittel

Versuchsvorschrift

As shown in step 4-v of Scheme 4, a mixture of 4,6-dichloropyrimidine (817 mg, 5.49 mmol), 2-(2-methoxyphenyl)-1-propanamine (0.997 g, 6.03 mmol), and DIEA (2.13 g, 2.87 mL, 16.5 mmol) in isopropanol (5.0 mL) was stirred for 18 hours. The reaction mixture was concentrated under reduced pressure and the residue purified by medium pressure chromatography on silica gel (25% EtOAc in hexanes) to give 6-chloro-N-(2-(2-methoxyphenyl)propyl)pyrimidin-4-amine as a colorless solid (Compound 2012, 1.18 g, 77% yield): 1H NMR (CDCl3) δ 8.31 (s, 1H), 7.23 (dd, J=12.0, 4.5 Hz, 2H), 7.03-6.87 (m, 2H), 6.41 (s, 1H), 5.42 (s, 1H), 3.89 (s, 3H), 3.67-3.18 (m, 3H), 1.35 (d, J=6.8 Hz, 3H).

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customthe residue purified by medium pressure chromatography on silica gel (25% EtOAc in hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-0b29956c3a2a4e19854f56dbdb02ba42
Quelldatensatz
uspto-grants-2016_06
Patentnummer
US09376448B2

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