Benzyl chloroformate → HCID 86725458, compound

HRID 2207124Notes

Reaction equation

HRID 2207124 reaction equation
[C:1]([C:5]1[N:10]=[C:9]([CH2:11][CH2:12][OH:13])[CH:8]=[C:7]([N:14]2[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]2)[N:6]=1)([CH3:4])([CH3:3])[CH3:2].C(N(CC)C(C)C)(C)C.Cl[C:30]([O:32][CH2:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)=[O:31]>C1COCC1.CC(=O)OCC>[CH2:33]([O:32][C:30]([N:17]1[CH2:16][CH2:15][N:14]([C:7]2[CH:8]=[C:9]([CH2:11][CH2:12][OH:13])[N:10]=[C:5]([C:1]([CH3:4])([CH3:2])[CH3:3])[N:6]=2)[CH2:19][CH2:18]1)=[O:31])[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1

Participants

6

Reactant 3

HCID 10387Benzyl chloroformateHCID 81531DiisopropylethylamineHCID 86725457HCID 86725457, compound

Product 1

HCID 86725458HCID 86725458, compoundYield 29.9%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2-tert-Butyl-4-(2-hydroxy-ethyl)-6-piperazin-1-yl-pyrimidine (5.1 g, 19.29 mmol) and N,N-diisopropylethylamine (7.48 g, 57.9 mmol) in THF (150 mL) was added benzyl chloroformate (CbzCl, 3.29 g, 19.29 mmol) dropwise at 0° C. The resulting mixture was stirred at room temperature overnight. The mixture was diluted with EA, washed with water, brine, dried over Na2SO4, filtered and concentrated to afford the crude title compound as an oil which was purified by column chromatography to afford the product (2.3 g, yield 29%) as a yellow oil.

Workup

  1. washwashed with water, brine
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customto afford the crude title compound as an oil which
  6. customwas purified by column chromatography

Sources & evidence

ORD record
ord-2ea488563e84488cba9570470a2a4959
Source dataset
uspto-grants-2016_06
Patent number
US09376396B2

Reaction notes

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