2,4-Dichloropyrimidine → Tert-butyl 4-(2-chloropyrimidin-4-yl)piperazine-1-carboxylate

HRID 2376651Notes

Reaction equation

HRID 2376651 reaction equation
[N:1]1([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.[Cl:14][C:15]1[N:20]=[C:19](Cl)[CH:18]=[CH:17][N:16]=1.C([O-])(O)=O.[Na+]>CCO>[Cl:14][C:15]1[N:20]=[C:19]([N:4]2[CH2:5][CH2:6][N:1]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH2:2][CH2:3]2)[CH:18]=[CH:17][N:16]=1

Participants

5

Reactant 3

HCID 775312,4-DichloropyrimidineHCID 143452tert-Butyl piperazine-1-carboxylateHCID 516892Sodium Bicarbonate

Product 1

HCID 11197306Tert-butyl 4-(2-chloropyrimidin-4-yl)piperazine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 9.55 g of tert-butyl 1-piperazinecarboxylate, 7.64 g of 2,4-dichloropyrimidine and 8.6 g of NaHCO3 in 50 ml of EtOH is heated at reflux for 1 hour. It is concentrated under vacuum, the residue is taken up in water and extracted with DCM, the organic phase is dried over Na2SO4 and the solvent is evaporated under vacuum. The residue is chromatographed on silica gel, eluting with a DCM/AcOEt (90/10 to 60/40; v/v) mixture. Two compounds are separated:

Workup

  1. temperatureis heated
  2. temperatureat reflux for 1 hour
  3. concentrationIt is concentrated under vacuum
  4. extractionextracted with DCM
  5. dry with materialthe organic phase is dried over Na2SO4
  6. customthe solvent is evaporated under vacuum
  7. customThe residue is chromatographed on silica gel
  8. washeluting with a DCM/AcOEt (90/10 to 60/40; v/v) mixture
  9. customTwo compounds are separated

Sources & evidence

ORD record
ord-9500ad0063f54084b120d9d9ec5dc024
Source dataset
uspto-grants-2008_12
Patent number
US07468368B2

Reaction notes

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