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

HRID 589916Notes

Reaction equation

HRID 589916 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-9d599c9f8cc444fd96bfaf2aad871f5d
Source dataset
uspto-grants-2016_01
Patent number
US09233969B2

Reaction notes

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