2-Chloropyrimidine → 3,5-Dimethyl-4-pyrimidin-2-ylpiperazine-1-carboxylic acid tert-butyl ester

HRID 76347Notes

Reaction equation

HRID 76347 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH:12]([CH3:14])[NH:11][CH:10]([CH3:15])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl[C:17]1[N:22]=[CH:21][CH:20]=[CH:19][N:18]=1>O>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH:12]([CH3:14])[N:11]([C:17]2[N:22]=[CH:21][CH:20]=[CH:19][N:18]=2)[CH:10]([CH3:15])[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 744042-ChloropyrimidineHCID 22219990Tert-butyl 3,5-dimethylpiperazine-1-carboxylate

Product 1

HCID 594069863,5-Dimethyl-4-pyrimidin-2-ylpiperazine-1-carboxylic acid tert-butyl esterYield 18.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

3,5-Dimethylpiperazine-1-carboxylic acid tert-butyl ester (1.676 g) and 2-chloropyrimidine (716 mg) were combined, melted in an oil bath at 120° C., and stirred for 5 hr 30 min. Water (10 ml) was added and the mixture was stirred, extracted with ethyl acetate (30 ml), and washed with saturated brine. The extract was dried over anhydrous sodium sulfate, and the solvent was evaporated. The obtained residue was purified by column chromatography (Yamazen HI-FLASH™ COLUMN size L, elution solvent: hexane/ethyl acetate) to give the title compound (333 mg).

Workup

  1. custommelted in an oil bath at 120° C.
  2. stirringthe mixture was stirred
  3. extractionextracted with ethyl acetate (30 ml)
  4. washwashed with saturated brine
  5. dry with materialThe extract was dried over anhydrous sodium sulfate
  6. customthe solvent was evaporated
  7. customThe obtained residue was purified by column chromatography (Yamazen HI-FLASH™ COLUMN size L, elution solvent: hexane/ethyl acetate)

Sources & evidence

ORD record
ord-cd96fb9f93694b3db7b4bb7b950145d4
Source dataset
uspto-grants-2014_09
Patent number
US08835631B2

Reaction notes

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