Hydrochloric Acid → 6-chloro-5-methyl-N-phenylpyrimidin-4-amine

HRID 241004

Reaktionsgleichung

Reaktionsgleichung von HRID 241004
Cl[C:2]1[C:7]([CH3:8])=[C:6]([Cl:9])[N:5]=[CH:4][N:3]=1.[NH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.Cl>C(O)(C)C>[Cl:9][C:6]1[N:5]=[CH:4][N:3]=[C:2]([NH:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:7]=1[CH3:8]

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 6115AnilineHCID 8188604,6-Dichloro-5-methylpyrimidine

Produkt 1

HCID 637349086-chloro-5-methyl-N-phenylpyrimidin-4-amineAusbeute 85,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3776IsopropanolLösungsmittel

Versuchsvorschrift

To a mixture of 4,6-dichloro-5-methylpyrimidine (2.27 g, 13.9 mmol) and aniline (1.0 g, 10.7 mmol) in isopropanol (15 mL) was added concentrated aqueous hydrochloric acid (1.5 mL) and heated to reflux for 2.5 h. The mixture was then concentrated and the residue triturated with ethyl acetate:isopropanol 4:1. The solid was collected by filtration and washed with additional ethyl acetate:isopropanol 4:1 then dried to give 6-chloro-5-methyl-N-phenylpyrimidin-4-amine (2.0 g, 67% yield). 1H NMR (400 MHz, d6-DMSO): 8.85 (s, 1H), 8.26 (s, 1H), 7.60 (d, 2H), 7.35 (tr, 2H), 7.11 (tr, 1H), 2.31 (s, 3H). MS (EI) for C11H10ClN3: 220 (MH+).

Aufarbeitung

  1. temperatureheated
  2. temperatureto reflux for 2.5 h
  3. concentrationThe mixture was then concentrated
  4. customthe residue triturated with ethyl acetate:isopropanol 4:1
  5. filtrationThe solid was collected by filtration
  6. washwashed with additional ethyl acetate:isopropanol 4:1
  7. customthen dried

Quellen und Nachweise

ORD-Eintrag
ord-22761ad4d6464744adf8f3738e887d43
Quelldatensatz
uspto-grants-2014_02
Patentnummer
US08648066B2

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