Phosphorus oxychloride → 4-chloro-7H-pyrrolo(2,3-d)pyrimidin-2-amine

Temperatur

110 °C

A mixture of 2-amino-7H-pyrrolo[2,3-d]pyrimidin-4-ol (Sigma, 150 mg, 1.0 mmol) in phosphorus oxychloride (1.5 mL) was heated at about 110° C. for about 30 minutes. Phosphorus oxychloride was carefully removed under reduced pressure and the reaction mixture was quenched by slow addition of ice water (10 mL). The resulting mixture was neutralized with saturated aqueous sodium carbonate (about 5 mL) to pH 7. The crude product was extracted into dichloromethane (20 mL) and washed with water (15 mL). The organic layer was separated and the aqueous phase was further extracted with dichloromethane (3×30 mL). The combined organic extracts were dried over anhydrous sodium sulfate and concentrated to give 4-chloro-7H-pyrrolo[2,3-d]pyrimidin-2-ylamine (0.036 g, 0.21 mmol) as a light yellow solid; LC/MS (Table 1, Method a) Rt 1.17 min; MS m/z: (M+H)+ 169.

1. customPhosphorus oxychloride was carefully removed under reduced pressure
2. customthe reaction mixture was quenched by slow addition of ice water (10 mL)
3. extractionThe crude product was extracted into dichloromethane (20 mL)
4. washwashed with water (15 mL)
5. customThe organic layer was separated
6. extractionthe aqueous phase was further extracted with dichloromethane (3×30 mL)
7. dry with materialThe combined organic extracts were dried over anhydrous sodium sulfate
8. concentrationconcentrated

ORD-Eintrag

ord-749f6d8f51ba451a832b255b914fd685

Quelldatensatz

uspto-grants-2011_08

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08008481B2