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

HRID 386097Notes

Reaction equation

HRID 386097 reaction equation
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

Participants

4

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-fca2c05b05df4e498bb5b4eca8f8a26c
Source dataset
uspto-grants-2013_02
Patent number
US08367706B2

Reaction notes

Loading…