Triethylamine → 5-Methoxy-2-piperazin-1-yl-pyrimidine hydrochloride

HRID 84764Notes

Reaction equation

HRID 84764 reaction equation
C(O[C:6]([N:8]1[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1)=O)(C)(C)C.[Cl:14]C1[N:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][N:16]=1.C(N(CC)CC)C>CN(C=O)C>[ClH:14].[CH3:22][O:21][C:18]1[CH:17]=[N:16][C:6]([N:8]2[CH2:9][CH2:10][NH:11][CH2:12][CH2:13]2)=[N:20][CH:19]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 143452tert-Butyl piperazine-1-carboxylateHCID 5890582-Chloro-5-methoxypyrimidine

Product 1

HCID 866866095-Methoxy-2-piperazin-1-yl-pyrimidine hydrochlorideYield 51.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

1.5 g piperazine-1-carboxylic acid tert-butyl ester was added to 1.2 g 2-chlor-5-methoxy-pyrimidine and 2.2 mL triethylamine in 30 mL DMF. The reaction was stirred 6 days at 60° C. The solvent was removed and the residue was dissolved in dichlormethane and extracted with water. The organic layer was washed with a saturated sodiumchloride-solution and evaporated. The residue was purified by HPLC to give 957 mg desired product.

Workup

  1. customThe solvent was removed
  2. dissolutionthe residue was dissolved in dichlormethane
  3. extractionextracted with water
  4. washThe organic layer was washed with a saturated sodiumchloride-solution
  5. customevaporated
  6. customThe residue was purified by HPLC

Sources & evidence

ORD record
ord-ead407df16ec434db4c7c75237acbeef
Source dataset
uspto-grants-2014_09
Patent number
US08846948B2

Reaction notes

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