Reaktion #1918644

ord-0a1aca006ea24e61ae7b7c3a54cd4258

Reaktionsgleichung

Nc1nc2nc(SCc3ccccc3)nc(Cl)c2s1
5-Phenylmethylthio-7-chloro-thiazolo[4,5-d]pyrimidin-2-ylamin
CCCCC(N)CO
DL-2-amino-1-hexanol
O=C([O-])[O-].[K+].[K+]
potassium carbonate
CCCCC(CO)Nc1nc(SCc2ccccc2)nc2nc(N)sc12
title compound
Ausbeute 17.6%
CCCCC(CO)Nc1nc(SCc2ccccc2)nc2nc(N)sc12
(±)-2-(2-Amino-5-phenylmethylthio-thiazolo[4,5-d]pyrimidin-7-ylamino)-hexan-1-ol
Ausbeute 17.6%

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    FiltrationThe solution was filtered
  2. 2
    Sonstigethe solvent was evaporated
  3. 3
    Sonstigechromatographed on silica (gradient eluent—ammonia:ethylacetate:dichloromethane, 1:69:30 to 1:99:0)

Vorschrift

5-Phenylmethylthio-7-chloro-thiazolo[4,5-d]pyrimidin-2-ylamin (100 mg, 0.32 mmol), DL-2-amino-1-hexanol (295 μL, 2.3 mmol) and potassium carbonate (124 mg, 0.90 mmol) were heated for 24 hours as in Example 1. The solution was filtered and the solvent was evaporated. The crude product was flash chromatographed on silica (gradient eluent—ammonia:ethylacetate:dichloromethane, 1:69:30 to 1:99:0) resulting in 22 mg (17% yield) of the title compound as a yellow solid.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US07067657B2uspto-grants-2006_06