Diisopropylethylamine → tert-Butyl 4-(5-bromopyrimidin-2-yl)piperazine-1-carboxylate

HRID 2366834Notes

Reaction equation

HRID 2366834 reaction equation
[N:1]1([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.[Br:14][C:15]1[CH:16]=[N:17][C:18](Cl)=[N:19][CH:20]=1.CCN(C(C)C)C(C)C>C(O)(C)(C)C>[Br:14][C:15]1[CH:16]=[N:17][C:18]([N:4]2[CH2:5][CH2:6][N:1]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH2:2][CH2:3]2)=[N:19][CH:20]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 143452tert-Butyl piperazine-1-carboxylateHCID 6066655-Bromo-2-chloropyrimidine

Product 1

HCID 21914476tert-Butyl 4-(5-bromopyrimidin-2-yl)piperazine-1-carboxylateYield 96.3%

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Conditions

Temperature
150 °C

Procedure

In a microwave vial were mixed: 1,1-dimethylethyl 1-piperazinecarboxylate (110 mg, 0.589 mmol, available from Fluke), 5-bromo-2-chloropyrimidine (95 mg, 0.491 mmol, available from Lancaster) and DIPEA (0.112 mL, 0.638 mmol) in tert-butanol (2 mL). The reaction was stirred and heated in an Emrys Optimizer microwave at 150° C. for 0.5 hr. The reaction mixture was partitioned between EtOAc (20 mL) and water (20 mL) and the organic layer washed with brine (20 mL) before being dried through an hydrophobic frit and concentrated to yield the desired product (162.3 mg)

Workup

  1. additionIn a microwave vial were mixed
  2. customThe reaction mixture was partitioned between EtOAc (20 mL) and water (20 mL)
  3. washthe organic layer washed with brine (20 mL)
  4. custombefore being dried through an hydrophobic frit
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-4a21dd4a9b0e433cabd71c7fa5921482
Source dataset
uspto-grants-2014_04
Patent number
US08697725B2

Reaction notes

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