Sulfoxonium, trimethyl-, iodide (1:1) → Tert-butyl 4-(5-(1-phenylcyclopropyl)pyrimidin-2-yl)piperazine-1-carboxylate

HRID 522693Notes

Reaction equation

[C:1]1([C:7]([C:9]2[CH:10]=[N:11][C:12]([N:15]3[CH2:20][CH2:19][N:18]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:17][CH2:16]3)=[N:13][CH:14]=2)=[CH2:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[I-].[CH3:29][S+](C)(C)=O>C1COCC1.CS(C)=O.C(OCC)(=O)C>[C:1]1([C:7]2([C:9]3[CH:14]=[N:13][C:12]([N:15]4[CH2:16][CH2:17][N:18]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:19][CH2:20]4)=[N:11][CH:10]=3)[CH2:29][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of tert-butyl 4-(5-(1-phenylvinyl)pyrimidin-2-yl)piperazine-1-carboxylate (366 mg, 1.0 mmol) in THF (20 mL) was added trimethylsulfoxonium iodide (1.1 g 5.0 mmol) in dimethyl sulfoxide (7 mL). The reaction mixture was stirred at 80° C. for 4 days, and diluted with ethyl acetate (200 mL). The organic phase was washed with water (200 mL) and brine (100 mL), dried over sodium sulfate, and concentrated. The residue was purified by silica gel chromatography (petroleum ether:ethyl acetate=20:1) to give tert-butyl 4-(5-(1-phenylcyclopropyl)pyrimidin-2-yl)piperazine-1-carboxylate (40 mg, 10%) as a yellow solid. MS (ES+) C22H28N4O2 requires: 380, found: 381 [M+H]+.

Workup

washThe organic phase was washed with water (200 mL) and brine (100 mL)
dry with materialdried over sodium sulfate
concentrationconcentrated
customThe residue was purified by silica gel chromatography (petroleum ether:ethyl acetate=20:1)

Sources & evidence

ORD record: ord-05b0bdd290d942239bcea83c4f5ab51d
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09334263B2

Reaction notes

Loading…