(Quinolin-2-yl)methanamine dihydrochloride → 4-Chloro-6-(2-furyl)-5-methylpyrimidine-2-amine

HRID 1356013

Reaktionsgleichung

Reaktionsgleichung von HRID 1356013
[NH2:1][C:2]1[N:7]=[C:6](OS(C(F)(F)F)(=O)=O)[C:5]([CH3:16])=[C:4]([C:17]2[O:18][CH:19]=[CH:20][CH:21]=2)[N:3]=1.[ClH:22].Cl.NCC1C=CC2C(=CC=CC=2)N=1>COCCOC>[Cl:22][C:6]1[C:5]([CH3:16])=[C:4]([C:17]2[O:18][CH:19]=[CH:20][CH:21]=2)[N:3]=[C:2]([NH2:1])[N:7]=1

Komponenten

4

Edukt 2

HCID 18507294(Quinolin-2-yl)methanamine dihydrochlorideHCID 86583753Trifluoromethanesulfonic acid 2-amino-6-furan-2-yl-5-methyl-pyrimidin-4-yl ester

Produkt 1

HCID 185072434-Chloro-6-(2-furyl)-5-methylpyrimidine-2-amineAusbeute 50 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 80711,2-DimethoxyethaneLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

To a stirred solution of 250 mg (0.77 mmol) trifluoromethanesulfonic acid 2-amino-6-furan-2-yl-5-methyl-pyrimidin-4-yl ester in 10 ml DME was added 489 mg (2.12 mmol) 2-(aminomethyl)quinoline dihydrochloride and the mixture heated at 80° C. for 16 hours. The reaction mixture was then concentrated in vacuo. Chromatography (ethyl acetate/hexane 4/1) followed by trituration in ether/hexane afforded 80 mg (50%) 4-chloro-6-furan-2-yl-5-methyl-pyrimidin-2-ylamine as a white crystalline solid. ES-MS m/e (%): 212 (M{37Cl}+H+, 50), 210 (M{35Cl}+H+, 100).

Aufarbeitung

  1. concentrationThe reaction mixture was then concentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-c977743f553b4ed087bc3a24d77fb843
Quelldatensatz
uspto-grants-2003_07
Patentnummer
US06586441B2

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