Reaktion #322250

Reaktionsgleichung

3-amino-2-carbomethoxy-5-chlorothieno[3,2-b]pyridine

sodium methoxide

→

title compound

3-Amino-2-carbomethoxy-5-methoxythieno[3,2-b]pyridine

Lösungsmittel

MeOH

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturwere refluxed for 18 h
2. 2
   EinengenThe reaction was concentrated
3. 3
   Sonstigepartitioned between EtOAc and NaHCO3 solution
4. 4
   TrocknenThe EtOAc layer was dried (MgSO4)
5. 5
   Filtrationfiltered
6. 6
   Einengenconcentrated
7. 7
   Sonstigechromatographed (5:1 hex: EtOAc)

Vorschrift

A solution of 3-amino-2-carbomethoxy-5-chlorothieno[3,2-b]pyridine, prepared as described in Example 62A (5g, 21 mmol) and sodium methoxide (4.5 g, 82 mmol) in MeOH (150 mL) were refluxed for 18 h. The reaction was concentrated and partitioned between EtOAc and NaHCO3 solution. The EtOAc layer was dried (MgSO4), filtered, concentrated, and chromatographed (5:1 hex: EtOAc) to yield 2.5 g of the title compound: 1H NMR (300 MHz, CDCl3) δ3.80 (s, 3H), 4.02 (s, 3H), 6.05 (bs, 2H), 6.89 (d, 1H), 7.88 (d, 1H); MS (DCI/NH3) m/e 239 (M+H)+.

Quelle