Reaktion #59241

ord-75161279d5f446eca4ddbf1e9bf8f6b3

Reaktionsgleichung

C[C@@]1(O)[C@H](O)[C@@H](CO)O[C@H]1n1ccc2c(NO)ncnc21
Nucleoside
C[C@@]1(O)[C@H](O)[C@@H](CO)O[C@H]1n1ccc2c(NO)ncnc21
7-(2′-C-methyl-β-D-ribofuranosyl)-4-hydroxylamino-pyrrolo[2,3-d]pyrimidine
O=C1CCC(=O)N1Cl
NCS
→
C[C@@]1(O)[C@H](O)[C@@H](CO)O[C@H]1n1cc(Cl)c2c(NO)ncnc21
123
C[C@@]1(O)[C@H](O)[C@@H](CO)O[C@H]1n1cc(Cl)c2c(NO)ncnc21
7-(2′-C-methyl-β-D-ribofuranosyl)-5-chloro-4-hydroxylamino-pyrrolo[2,3-d]pyrimidine

Edukte

C[C@@]1(O)[C@H](O)[C@@H](CO)O[C@H]1n1ccc2c(NO)ncnc21
Nucleoside
C[C@@]1(O)[C@H](O)[C@@H](CO)O[C@H]1n1ccc2c(NO)ncnc21
7-(2′-C-methyl-β-D-ribofuranosyl)-4-hydroxylamino-pyrrolo[2,3-d]pyrimidine
O=C1CCC(=O)N1Cl
NCS

Reagenzien

Keine

Lösungsmittel

CN(C)C=O
DMF
CN(C)C=O
DMF

Reaktionsbedingungen

Temperatur
0°CELSIUS
Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    workup.ADDITIONis then added dropwise
  2. 2
    SonstigeThe reaction is quenched with methanol (5 mL)
  3. 3
    Einengenconcentrated

Vorschrift

Nucleoside 117 (0.1 mmol) is dissolved in DMF (0.5 mL) and cooled to 0° C. NCS (0.1 mmol) dissolved in DMF (0.5 mL) is then added dropwise and the reaction stirred for 30 minutes at 0° C. and 30 minutes at room temperature. The reaction is quenched with methanol (5 mL) and then concentrated. Column chromatography (SiO2) with MeOH/DCM affords 123.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US07425547B2uspto-grants-2008_09