Triethylamine → Tert-butyl 4-(6-methoxypyrimidin-4-yl)piperazine-1-carboxylate

HRID 68550Notes

Reaction equation

HRID 68550 reaction equation
C(N(CC)CC)C.[C:8]([O:12][C:13]([N:15]1[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]1)=[O:14])([CH3:11])([CH3:10])[CH3:9].Cl[C:22]1[CH:27]=[C:26]([O:28][CH3:29])[N:25]=[CH:24][N:23]=1>CN(C=O)C>[C:8]([O:12][C:13]([N:15]1[CH2:20][CH2:19][N:18]([C:22]2[CH:27]=[C:26]([O:28][CH3:29])[N:25]=[CH:24][N:23]=2)[CH2:17][CH2:16]1)=[O:14])([CH3:11])([CH3:9])[CH3:10]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 143452tert-Butyl piperazine-1-carboxylateHCID 10515094-Chloro-6-methoxypyrimidine

Product 1

HCID 66569709Tert-butyl 4-(6-methoxypyrimidin-4-yl)piperazine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

18.6 mL triethylamine and piperazine-1-carboxylic acid tert-butyl ester were added to 9.7 g 4-chloro-6-methoxy-pyrimidine in 50 mL DMF. The reaction was stirred over night at 60° C. The reaction was cooled and the precipitate was filtered. The filtrate was evaporated. The residue was dissolved in DCM, extracted with water and washed with sodium chloride solution. The solvent was evaporated and the residue was crystallized with a mixture of petrolether and diethylether (8:2) to yield 8.7 g of the desired compound.

Workup

  1. temperatureThe reaction was cooled
  2. filtrationthe precipitate was filtered
  3. customThe filtrate was evaporated
  4. dissolutionThe residue was dissolved in DCM
  5. extractionextracted with water
  6. washwashed with sodium chloride solution
  7. customThe solvent was evaporated
  8. customthe residue was crystallized with a mixture of petrolether and diethylether (8:2)

Sources & evidence

ORD record
ord-480b9947a2fb41b6ab3655deb9dd0a1b
Source dataset
uspto-grants-2014_09
Patent number
US08822464B2

Reaction notes

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