Diisopropylethylamine → tert-Butyl 4-(6-chloro-2-methylpyrimidin-4-yl)piperazine-1-carboxylate

HRID 885948Notes

Reaction equation

Cl[C:2]1[CH:7]=[C:6]([Cl:8])[N:5]=[C:4]([CH3:9])[N:3]=1.[N:10]1([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]1.CCN(C(C)C)C(C)C>C1COCC1>[C:19]([O:18][C:16]([N:10]1[CH2:15][CH2:14][N:13]([C:2]2[CH:7]=[C:6]([Cl:8])[N:5]=[C:4]([CH3:9])[N:3]=2)[CH2:12][CH2:11]1)=[O:17])([CH3:22])([CH3:20])[CH3:21]

Participants

Conditions

Temperature: 145 °C

Procedure

To a solution of 4,6-dichloro-2-methylpyrimidine (300 mg, 1.84 mmol) in THF (4 mL) were added tert-butyl piperazine-1-carboxylate (376 mg, 2.02 mmol) and DIPEA (0.48 mL, 2.76 mmol), and the reaction was heated at 145° C. under microwave irradiation for 30 minutes. The resulting mixture was concentrated in vacuo and the residue was partitioned between DCM (50 mL) and water (50 mL). The organic fraction was washed with brine (50 mL), dried (MgSO4) and concentrated in vacuo to yield the title compound (400 mg, 70%) as an off-white solid. LCMS (ES+) 313.0 (M+H)+, RT 3.63 minutes (Method 1).

Workup

concentrationThe resulting mixture was concentrated in vacuo
customthe residue was partitioned between DCM (50 mL) and water (50 mL)
washThe organic fraction was washed with brine (50 mL)
dry with materialdried (MgSO4)
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-e44c80a8f21040098563cb4f3baa8886
Source dataset: uspto-grants-2012_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08242116B2

Reaction notes

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