Reacción #332744

Ecuación de reacción

7-chloro-6-((2R,6S)-2,6-dimethylmorpholino)-3-methylisoxazolo[4,5-b]pyridine-5-carbaldehyde

Intermediate 471

7-chloro-6-((2R,6S)-2,6-dimethylmorpholino)-3-methylisoxazolo[4,5-b]pyridine-5-carbaldehyde

pyrimidine-2,4,6(1H,3H,5H)-trione

→

yellow solid

Rendimiento 42.7%

(2R,4S,4aS)-rel-11-Chloro-2,4,8-trimethyl-2,4,4a,6-tetrahydro-1H,1′H-spiro[isoxazolo[4,5-g][1,4]oxazino[4,3-a][1,5]naphthyridine-5,5′-pyrimidine]-2′,4′,6′(3′H)-trione

Rendimiento 42.7%

Disolventes

Isopropanol

Condiciones de reacción

Tratamiento posterior

1. 1
   Otroto give a yellow slurry
2. 2
   Concentraciónthe mixture was concentrated
3. 3
   OtroThe crude was purified by chromatography

Procedimiento

Isopropanol (12 ml) was added to 7-chloro-6-((2R,6S)-2,6-dimethylmorpholino)-3-methylisoxazolo[4,5-b]pyridine-5-carbaldehyde (Intermediate 471, 165 mg, 0.53 mmol) to give a yellow slurry; pyrimidine-2,4,6(1H,3H,5H)-trione (barbituric acid) (68.2 mg, 0.53 mmol) was added, and the mixture was heated to 80° C. After about 5 days, the mixture was concentrated. The crude was purified by chromatography using 10-50% EtOAc/CH2Cl2 to give 95 mg yellow solid which was subsequently recrystallized from EtOAc/hexanes. A total of 57 mg (19%) of the title product was obtained as a yellow solid.

Fuente