tert-Butyl piperazine-1-carboxylate → 1,1-Dimethylethyl 4-(5-iodo-2-pyrazinyl)-1-piperazinecarboxylate

HRID 2366830Notes

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[C:15]1[CH:20]=[N:19][C:18]([I:21])=[CH:17][N:16]=1>C(O)(C)(C)C>[I:21][C:18]1[N:19]=[CH:20][C:15]([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:16][CH:17]=1

Participants

Conditions

Temperature: 100 °C

Procedure

In a 5 mL round bottomed flask were mixed: 1,1-dimethylethyl 1-piperazinecarboxylate (110 mg, 0.590 mmol, available from Fluke), 2-bromo-5-iodopyrazine (140 mg, 0.491 mmol, available from Apollo) and Dipea (0.112 mL, 0.639 mmol) in Tert-Butanol (2 mL). The reaction was stirred and heated under reflux at 100° C. for 40 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. The samples were dissolved in 1:1 MeOH:DMSO 2×1 mL and purified by MDAP. The solvent was evaporated in vacuo to give the required product 1,1-dimethylethyl 4-(5-iodo-2-pyrazinyl)-1-piperazinecarboxylate (98.6 mg) LCMS (Method C): Rt=1.20, MH+=391

Workup

additionIn a 5 mL round bottomed flask were mixed
temperatureheated
customThe reaction mixture was partitioned between EtOAc (20 mL) and water (20 mL)
washthe organic layer washed with brine (20 mL)
custombefore being dried through an hydrophobic frit
concentrationconcentrated
dissolutionThe samples were dissolved in 1:1 MeOH
customDMSO 2×1 mL and purified by MDAP
customThe solvent was evaporated in vacuo

Sources & evidence

ORD record: ord-73bd7c554b554ae8928eb9e01835ee4e
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08697725B2

Reaction notes

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