Reacción #309342

Ecuación de reacción

(1S,2S,4R)-4-{4-[(1R)-2,3-Dihydro-1H-inden-1-ylamino]-7H-pyrrolo[2,3-d]-pyrimidin-7-yl}-2-(hydroxymethyl)cyclopentanol

2,6-di-tert-butyl-4-methylpyridine

tert-Butyl (chlorosulfonyl)carbamate

→

title compound

Rendimiento 37.0%

tert-Butyl{[((1S,2S,4R)-4-{4-[(1R)-2,3-Dihydro-1H-inden-1-ylamino]-7H-pyrrolo-[2,3-d]pyrimidin-7-yl}-2-hydroxycyclopentyl)methoxy]sulfonyl}carbamate

Rendimiento 37.0%

Disolventes

AcCN

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.ADDITIONwas added
2. 2
   OtroThe reaction was quenched via addition of MeOH (1.00 mL)
3. 3
   Concentraciónconcentrated in vacuo
4. 4
   LavadoSilica gel chromatography eluting with a gradient of 0 to 10% MeOH in DCM

Procedimiento

(1S,2S,4R)-4-{4-[(1R)-2,3-Dihydro-1H-inden-1-ylamino]-7H-pyrrolo[2,3-d]-pyrimidin-7-yl}-2-(hydroxymethyl)cyclopentanol (27.6 mg, 0.117 mmol) and 2,6-di-tert-butyl-4-methylpyridine (48.5 mg, 0.236 mmol) were suspended in AcCN (1.57 mL) and cooled to 0° C. tert-Butyl (chlorosulfonyl)carbamate was added and the mixture was allowed to warm to rt overnight. The reaction was quenched via addition of MeOH (1.00 mL) and concentrated in vacuo. Silica gel chromatography eluting with a gradient of 0 to 10% MeOH in DCM afforded the title compound (15.2 mg, 37%). LC/MS: Rt=1.29 min, ES+ 544 (FA standard).

Fuente