Reaktion #1484343

Reaktionsgleichung

4-aminobenzonitrile

LiHMDS

1-(4′-(cyclopropylmethyl)-2-(methylsulfinyl)-4,5′-bipyrimidin-2′-ylamino)-2-methylpropan-2-ol

→

desired product

Ausbeute 28.0%

4-(4′-(cyclopropylmethyl)-2′-(2-hydroxy-2-methylpropylamino)-4,5′-bipyrimidin-2-ylamino)benzonitrile

Ausbeute 28.0%

Lösungsmittel

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturTo the reaction mixture cooled back to −78° C.
2. 2
   Temperaturthe reaction mixture was warmed up to rt
3. 3
   workup.STIRRINGwas stirred for additional 1 hour
4. 4
   SonstigeThe crude product was purified by reverse-phase HPLC [30-100% organic phase over 15 minutes]

Vorschrift

To a solution of 4-aminobenzonitrile (16.34 mg, 0.138 mmol) in THF (277 μl) cooled to −78° C. under nitrogen, LiHMDS (415 μl, 0.415 mmol) was added dropwise. The reaction mixture was warmed up to rt, then was stirred for 30 minutes. To the reaction mixture cooled back to −78° C., 1-(4′-(cyclopropylmethyl)-2-(methylsulfinyl)-4,5′-bipyrimidin-2′-ylamino)-2-methylpropan-2-ol (5-3) (50 mg, 0.138 mmol) was added, and the reaction mixture was warmed up to rt, then was stirred for additional 1 hour. According to LC/MS, the reaction was complete. The crude product was purified by reverse-phase HPLC [30-100% organic phase over 15 minutes] followed by Biotage™ silica gel chromatography [10 g SNAP column, 100% DCM to 12% MeOH/DCM] to obtain the desired product (16 mg, 28%).

Quelle