Reaktion #509178

Reaktionsgleichung

4-chloro-5-iodo-6-methylpyrimidin-2-amine

triethylamine

4-aminotetrahydropyran HCl salt

→

5-iodo-6-methyl-N4-(tetrahydro-2H-pyran-4-yl)pyrimidine-2,4-diamine

Ausbeute 51.7%

Lösungsmittel

EtOH

H2O

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe reaction was heated
2. 2
   Temperaturto reflux
3. 3
   SonstigeAbout 80% of the solvent was evaporated under reduced pressure
4. 4
   SonstigeThe mixture was partitioned between ethyl acetate and H2O
5. 5
   TrocknenThe organic layer was dried over anhydrous sodium sulfate
6. 6
   Einengenconcentrated in vacuo
7. 7
   Sonstigeto afford the crude product
8. 8
   SonstigeThe product was purified by a flash chromatography (50% ethyl acetate/hexanes to 100% ethyl acetate)

Vorschrift

To a suspension of 4-chloro-5-iodo-6-methylpyrimidin-2-amine (16.0 g, 59.3 mmol) in EtOH (200 mL) and H2O (250 mL) was added triethylamine (30.0 mL, 207.5 mmol) and 4-aminotetrahydropyran HCl salt (9.75 g, 71.2 mmol) successively. The reaction was heated to reflux, stirred for 72 h, and then cooled to RT. About 80% of the solvent was evaporated under reduced pressure. The mixture was partitioned between ethyl acetate and H2O. The organic layer was dried over anhydrous sodium sulfate and concentrated in vacuo to afford the crude product. The product was purified by a flash chromatography (50% ethyl acetate/hexanes to 100% ethyl acetate) to afford 5-iodo-6-methyl-N4-(tetrahydro-2H-pyran-4-yl)pyrimidine-2,4-diamine as a light yellow crystal (yield: 10.23 g, 51.7%). LC/MS: calculated for C10H15IN4O (334.03). found: 335.08 (MH+). HPLC analytical purity: >99.0%.

Quelle