Reaktion #11068

Reaktionsgleichung

intermediate 1g

tert-butyl (S)-3-{[(benzyloxy)carbonyl]amino}-4-oxo-4,6,7,8-tetrahydropyrrolo[1,2-a]pyrimidine-6-carboxylate

MeI

→

intermediate 19a

Ausbeute 160.9%

3-benzyloxycarbonylamino-6-methyl-4-oxo-4,6,7,8-tetrahydro-pyrrolo[1,2-a]pyrimidine-6-carboxylic acid tert-butyl ester

Ausbeute 160.9%

Lösungsmittel

THF

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGThe mixture was stirred
2. 2
   Sonstigewas quenched with sat. NH4Cl
3. 3
   workup.ADDITIONThe mixture was diluted with EtOAc
4. 4
   Waschenwashed with H2O and brine
5. 5
   Trocknendried (Na2SO4)
6. 6
   Einengenconcentrated
7. 7
   SonstigeThe resultant residue was combined with additional crude material from another batch for purification by flash chromatography (stepwise gradient, 40 to 45 to 50% EtOAc/hexanes)

Vorschrift

To a solution of intermediate 1g (200 mg, 0.519 mmol) in 5 mL THF at −78° C., was added a 1M solution of LIHMDS in THF (1.09 mL, 1.09 mmol). The mixture was stirred for 5 min, then MeI (162 mL, 2.60 mmol) was added. The mixture was stirred with warming to −30° C. over 1 h, then was quenched with sat. NH4Cl. The mixture was diluted with EtOAc and washed with H2O and brine, dried (Na2SO4), and concentrated. The resultant residue was combined with additional crude material from another batch for purification by flash chromatography (stepwise gradient, 40 to 45 to 50% EtOAc/hexanes) to afford 59 mg of intermediate 19a (18%, based on 0.835 mmol of starting material). LR MS.

Quelle