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

HRID 1428936Notes

Reaction equation

HRID 1428936 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl[C:15]1[CH:20]=[C:19]([O:21][CH3:22])[N:18]=[CH:17][N:16]=1.C(N(CC)CC)C>CN(C=O)C.O>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:15]2[CH:20]=[C:19]([O:21][CH3:22])[N:18]=[CH:17][N:16]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

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-carboxylateYield 58%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

10.8 g piperazine-1-carboxylic acid tert-butyl ester was added to 8.3 g 4-chloro-6-methoxy-pyrimidine and 16 mL triethylamine in 40 mL DMF. The reaction was stirred over night at 60° C. The mixture was diluted with water and extracted with ethyl acetate. The organic layer was dried with magnesium sulfate and evaporated. The residue was purified chromatography on silica gel (petrolether/ethyl acetate: 8/2) to yield 9.8 g of the desired compound.

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe organic layer was dried with magnesium sulfate
  3. customevaporated
  4. customThe residue was purified chromatography on silica gel (petrolether/ethyl acetate: 8/2)

Sources & evidence

ORD record
ord-56fec579ac164c639bb319f0dbf82384
Source dataset
uspto-grants-2015_01
Patent number
US08937176B2

Reaction notes

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