Reaktion #167991

Reaktionsgleichung

(R)-6-benzyl-2-(3-methyl-1-tosyl-1H-indol-4-yl)-4-(3-methyl-4-((2-nitrophenyl)sulfonyl)piperazin-1-yl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine

1-chloroethyl carbonochloridate

→

(R)-2-(3-methyl-1-tosyl-1H-indol-4-yl)-4-(3-methyl-4-((2-nitrophenyl)sulfonyl)piperazin-1-yl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine

Lösungsmittel

MeCN

Reaktionsbedingungen

Aufarbeitung

1. 1
   Einengenwas concentrated in vacuo
2. 2
   workup.DISSOLUTIONThe resulting residue was dissolved in a 2:1 mixture of dichloromethane
3. 3
   workup.WAITplaced at room temperature for ca. 15 h
4. 4
   workup.ADDITIONThe mixture was then diluted with dichloromethane and saturated aqueous sodium bicarbonate
5. 5
   SonstigeThe layers were separated
6. 6
   Extraktionthe aqueous layer was extracted two additional times with dichloromethane
7. 7
   TrocknenThe organic layers were combined dried over Na2SO4
8. 8
   Filtrationfiltered
9. 9
   Einengenconcentrated
10. 10
    SonstigeThe resulting residue was purified by silica gel flash chromatography (3-12% MeOH/DCM)

Vorschrift

To a solution of (R)-6-benzyl-2-(3-methyl-1-tosyl-1H-indol-4-yl)-4-(3-methyl-4-((2-nitrophenyl)sulfonyl)piperazin-1-yl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine (1.17 g, 1.47 mmol) in MeCN (15 mL) was added 1-chloroethyl carbonochloridate (0.18 mL, 1.62 mmol), and the mixture was stirred for 15 minutes at which time the mixture was concentrated in vacuo. The resulting residue was dissolved in a 2:1 mixture of dichloromethane:methanol (15 mL) and heated at 40° C. for 1 hour and then placed at room temperature for ca. 15 h. The mixture was then diluted with dichloromethane and saturated aqueous sodium bicarbonate. The layers were separated and the aqueous layer was extracted two additional times with dichloromethane. The organic layers were combined dried over Na2SO4, filtered and concentrated. The resulting residue was purified by silica gel flash chromatography (3-12% MeOH/DCM) to provide (R)-2-(3-methyl-1-tosyl-1H-indol-4-yl)-4-(3-methyl-4-((2-nitrophenyl)sulfonyl)piperazin-1-yl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine. MS (ESI+) m/z 702.3 (M+H)+.

Quelle