Phosphorus oxychloride → Ethyl 4-chloro-7H-pyrrolo[2,3-d]pyrimidine-6-carboxylate

HRID 567748

Reaktionsgleichung

Reaktionsgleichung von HRID 567748
[CH2:1]([O:3][C:4]([C:6]1[NH:15][C:9]2[N:10]=[CH:11][N:12]=[C:13](O)[C:8]=2[CH:7]=1)=[O:5])[CH3:2].O=P(Cl)(Cl)[Cl:18]>>[Cl:18][C:13]1[C:8]2[CH:7]=[C:6]([C:4]([O:3][CH2:1][CH3:2])=[O:5])[NH:15][C:9]=2[N:10]=[CH:11][N:12]=1

Komponenten

3

Edukt 2

HCID 24813Phosphorus oxychlorideHCID 178468549HCID 178468549, Verbindung

Produkt 1

HCID 21262606Ethyl 4-chloro-7H-pyrrolo[2,3-d]pyrimidine-6-carboxylate

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

Under a N2 atmosphere, 32.0 g (154 mmol) of 6-ethoxycarbonyl-4-hydroxy-7H-pyrrolo[2,3-d]pyrimidine are suspended in 308 ml (338 mmol) of POCl3 at RT and warmed to 120° C. with stirring; the solid dissolves in the course of this. After stirring at 120° C. for 3 h, the excess POCl3 is distilled off (65° C. external temperature; 15 mbar). Suspension of the residue in 50 ml of ice-cold toluene, filtration and washing with toluene yields 4-chloro-6-ethoxycarbonyl-7H-pyrrolo[2,3-d]pyrimidine; m.p. 219-221° C.; 1H-NMR (DMSO-d6) 8.77 and 7.24 (2s, 2H), 4.39 (q, J=7, 2H), 1.36 (t, J=7, 3H). Further product can be obtained from the evaporated filtrate by stirring in ethyl acetate/water.

Aufarbeitung

  1. dissolutionthe solid dissolves in the course of this
  2. stirringAfter stirring at 120° C. for 3 h
  3. distillationthe excess POCl3 is distilled off (65° C. external temperature; 15 mbar)
  4. additionSuspension of the residue in 50 ml of ice-cold toluene
  5. filtrationfiltration
  6. washwashing with toluene

Quellen und Nachweise

ORD-Eintrag
ord-0ca2d97762544cc28c8610914d33b466
Quelldatensatz
uspto-grants-2001_01
Patentnummer
US06180636B2

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