Hydrochloric Acid → 4-Chloro-7-(4-methoxybenzyl)-5H-pyrrolo[2,3-d]pyrimidin-6(7H)-one

HRID 1685192Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1685192
[Cl:1][C:2]1[C:7]([CH2:8][C:9](OC)=[O:10])=[C:6]([NH:13][CH2:14][C:15]2[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=2)[N:5]=[CH:4][N:3]=1.Cl.O>>[Cl:1][C:2]1[C:7]2[CH2:8][C:9](=[O:10])[N:13]([CH2:14][C:15]3[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=3)[C:6]=2[N:5]=[CH:4][N:3]=1

Komponenten

4

Edukt 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 86641609Methyl 2-(4-chloro-6-(4-methoxybenzylamino)pyrimidin-5-yl)acetate

Produkt 1

HCID 866416104-Chloro-7-(4-methoxybenzyl)-5H-pyrrolo[2,3-d]pyrimidin-6(7H)-oneAusbeute 76,4 %

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

Add a solution of methyl 2-(4-chloro-6-(4-methoxybenzylamino)pyrimidin-5-yl)acetate (16.21 g, 1.00 equiv; 50.38 mmol) to HCl (4M in dioxane) (126 mL; 10 equiv; 503.79 mmol) and water (4.54 mL; 5 equiv; 251.89 mmol) and stir at 100° C. for 2 h. Remove dioxane in vacuo and extract with EA. Wash the organic layer with saturated NaHCO3, water, then brine. Dry over MgSO4, filter and concentrate in vacuo. Purify the residue by ISCO 330 g using EA:hex 20 to 70% as eluent to obtain the title compound (11.15 g; 38.49 mmol; 76.39%) as a yellow solid. 1H NMR (300 MHz, DMSO): 8.65 (s, 1H), 7.29-7.26 (m, 2H), 6.89-6.85 (m, 2H), 4.79 (s, 2H), 3.80 (s, 2H), 3.71 (s, 3H).

Aufarbeitung

  1. extractionRemove dioxane in vacuo and extract with EA
  2. washWash the organic layer with saturated NaHCO3, water
  3. dry with materialDry over MgSO4
  4. filtrationfilter
  5. concentrationconcentrate in vacuo
  6. customPurify the residue by ISCO 330 g

Quellen und Nachweise

ORD-Eintrag
ord-6715b2f750b8489ca30caccf4e1c4ad4
Quelldatensatz
uspto-grants-2012_04
Patentnummer
US08148387B2

Notizen zur Reaktion

Wird geladen…