Reaktion #561471

Reaktionsgleichung

2-(allyloxy)-4-aminobenzonitrile

N-allyl-2-chloro-7-(4-fluorophenyl)-7-methyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-amine

H2SO4

→

4-(4-(allylamino)-7-(4-fluorophenyl)-6,7-dihydro-5H-cyclopenta[d]pyrimidin-2-ylamino)-2-(allyloxy)benzonitrile

Ausbeute 26.1%

Lösungsmittel

N-Methyl-2-pyrrolidinone

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe crude reaction mixture
2. 2
   Sonstigewas purified by PREP HPLC
3. 3
   workup.WAITto 100% A:B over 40 min
4. 4
   Sonstige3 min
5. 5
   EinengenThe appropriate fractions were concentrated in vacuo

Vorschrift

To a solution of 2-(allyloxy)-4-aminobenzonitrile (Preparation D, 168 mg, 0.963 mmol), and N-allyl-2-chloro-7-(4-fluorophenyl)-7-methyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-amine (Preparation Ua, 204 mg, 0.642 mmol) in N-Methyl-2-pyrrolidinone (5135 μL) was added H2SO4 (54.7 μL, 1.027 mmol). The mixture was stirred at 100° C. overnight. The crude reaction mixture was purified by PREP HPLC: (50×250 mm HPLC XTerra C18.15 to 100% A:B over 40 min, 3 min at 100% B (A is 90:10:0.1 water:MeOH:TFA; B is 90:10:0.1 MeOH:water:TFA)). The appropriate fractions were concentrated in vacuo to afford 4-(4-(allylamino)-7-(4-fluorophenyl)-6,7-dihydro-5H-cyclopenta[d]pyrimidin-2-ylamino)-2-(allyloxy)benzonitrile (74 mg, 25% yield). LC-MS (M+H)+=456.1.

Quelle