Reaktion #1179381

Reaktionsgleichung

(S)-ethyl 5-amino-6-(5-cyclopropyl-1H-pyrazol-3-ylamino)-2-[1-(4-fluorophenyl)ethylamino]pyrimidine-4-carboxylate

formamidine acetate

→

title compound

Ausbeute 9.5%

Ethyl 9-(5-cyclopropyl-1H-pyrazol-3-yl)-2-[(S)-1-(4-fluorophenyl)ethylamino]-9H-purine-6-carboxylate

Ausbeute 9.5%

Lösungsmittel

EtOH

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturwas heated
2. 2
   Temperaturto reflux for 12 hours
3. 3
   EinengenThe reaction was then concentrated
4. 4
   workup.DISSOLUTIONthe resulting residue was dissolved in EtOAc (50 ml)
5. 5
   Waschenwashed with saturated NaHCO3 solution (50 ml)
6. 6
   SonstigeThe organic layer was dried
7. 7
   Filtrationfiltered
8. 8
   Einengenconcentrated
9. 9
   SonstigeThe resulting solid was purified by column chromatography (DCM:MeOH=20:1)

Vorschrift

A mixture of (S)-ethyl 5-amino-6-(5-cyclopropyl-1H-pyrazol-3-ylamino)-2-[1-(4-fluorophenyl)ethylamino]pyrimidine-4-carboxylate (Method 47; 0.6 g, 1.4 mmol) and formamidine acetate (0.32 g, 3.1 mmol) in EtOH (20 ml) was heated to reflux for 12 hours. The reaction was then concentrated, and the resulting residue was dissolved in EtOAc (50 ml) and washed with saturated NaHCO3 solution (50 ml). The organic layer was dried, filtered, and concentrated. The resulting solid was purified by column chromatography (DCM:MeOH=20:1) to give the title compound (0.058 g, 8%). NMR (400 MHz, CD3OD) 8.48 (s, 1H), 7.45-7.41 (m, 2H), 7.03-6.99 (m, 2H), 6.25 (s, 1H), 5.12-5.03 (m, 1H), 4.50 (q, J=7.2 Hz, 2H), 2.00-1.96 (m, 1H), 1.54 (d, J=7.0 Hz, 3H), 1.44 (t, J=7.2 Hz, 3H), 1.10-1.08 (m, 2H), 0.81-0.74 (m, 2H). MS: Calcd.: 435; Found: [M+H]+ 436.

Quelle