Phosphorus oxychloride → 4-Chloro-2-(pyrrolidin-1-yl)pyrimidine

HRID 386097Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 386097
C(O[C:4]1[CH:9]=[CH:8][N:7]=[C:6]([N:10]2[CH2:14][CH2:13][CH2:12][CH2:11]2)[N:5]=1)C.O=P(Cl)(Cl)[Cl:17]>CN(C=O)C>[Cl:17][C:4]1[CH:9]=[CH:8][N:7]=[C:6]([N:10]2[CH2:14][CH2:13][CH2:12][CH2:11]2)[N:5]=1

Komponenten

4

Edukt 2

HCID 24813Phosphorus oxychlorideHCID 595258964-Ethoxy-2-pyrrolidin-1-ylpyrimidine

Produkt 1

HCID 104877204-Chloro-2-(pyrrolidin-1-yl)pyrimidine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

4-Ethoxy-2-pyrrolidin-1-ylpyrimidine (2.0 g, 10 mol) was added to 15 mL of POCl3, followed by the addition of 0.5 ml of DMF. The reaction mixture was irradiated under microwave at 160° C. for 1.5 h. Most of the solvent was evaporated in vacuo. The residue was added in portions to ice-water containing ammonia. The precipitate was filtered off. The aqueous filtrate was extracted with EtOAc. The organic phase was dried over sodium sulfate, filtered, and concentrated. The solid precipitate was combined with the crude residue and purified by silica gel column chromatography to afford the title compound.

Aufarbeitung

  1. customThe reaction mixture was irradiated under microwave at 160° C. for 1.5 h
  2. customMost of the solvent was evaporated in vacuo
  3. additionThe residue was added in portions to ice-water
  4. additioncontaining ammonia
  5. filtrationThe precipitate was filtered off
  6. extractionThe aqueous filtrate was extracted with EtOAc
  7. dry with materialThe organic phase was dried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated
  10. custompurified by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-fca2c05b05df4e498bb5b4eca8f8a26c
Quelldatensatz
uspto-grants-2013_02
Patentnummer
US08367706B2

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