Reaktion #711785

Reaktionsgleichung

DCM

water

5-Benzoyl-6-(bromomethyl)-1,3-dimethylpyrimidine-2,4(1H,3H)-dione

6-(2-Amino-ethyl)-1,3-dimethyl-5-phenyl-1,6-dihydro-pyrrolo[3,4-d]pyrimidine-2,4-dione

Intermediate A

6-(2-Amino-ethyl)-1,3-dimethyl-5-phenyl-1,6-dihydro-pyrrolo[3,4-d]pyrimidine-2,4-dione

ethanolamine

ethanolamine

→

6-(2-Hydroxyethyl)-1,3-dimethyl-5-phenyl-1H-pyrrolo[3,4-d]pyrimidine-2,4(3H,6H)-dione

Lösungsmittel

EtOH

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturheating
2. 2
   SonstigeThe layers were separated
3. 3
   Extraktionthe aqueous phase extracted with DCM (2×50 mL)
4. 4
   WaschenThe combined organic phases were washed with water (2×50 mL)
5. 5
   SonstigeThe solvent was removed under reduced pressure
6. 6
   Sonstigeaffording a pale yellow solid
7. 7
   SonstigeThe solid was triturated in hot EtOH
8. 8
   Temperaturto cool
9. 9
   FiltrationThe title product was collected by reduced pressure filtration as a white powder

Vorschrift

5-Benzoyl-6-(bromomethyl)-1,3-dimethylpyrimidine-2,4(1H,3H)-dione (Intermediate A step 3) (400 mg 1.19 mmol) in EtOH (4 mL) was treated with TEA (0.16 mL, 1.19 mmol) and ethanolamine (72.5 mg, 1.19 mmol). The mixture was heated to 100° C. for 1 h under microwave irradiation. A further portion of ethanolamine (96 μL) was added and heating continued for a further 20 min. The reaction was poured into DCM (75 mL) and water (75 mL). The layers were separated and the aqueous phase extracted with DCM (2×50 mL). The combined organic phases were washed with water (2×50 mL), then passed through a hydrophobic frit. The solvent was removed under reduced pressure affording a pale yellow solid. The solid was triturated in hot EtOH and allowed to cool. The title product was collected by reduced pressure filtration as a white powder.

Quelle