Dimethyl Sulfoxide → HCID 59484996, compound

HRID 1850503Notes

Reaction equation

CS(C)=O.[CH3:5][C:6]1([CH3:24])[CH2:10][C:9]2[C:11]([CH3:23])=[C:12]([N:17]3[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]3)[C:13]([CH3:16])=[C:14]([CH3:15])[C:8]=2[O:7]1.Br[C:26]1[N:31]=[CH:30][CH:29]=[CH:28][N:27]=1.C(N(C(C)C)CC)(C)C>C(OCC)(=O)C>[CH3:5][C:6]1([CH3:24])[CH2:10][C:9]2[C:11]([CH3:23])=[C:12]([N:17]3[CH2:18][CH2:19][N:20]([C:26]4[N:31]=[CH:30][CH:29]=[CH:28][N:27]=4)[CH2:21][CH2:22]3)[C:13]([CH3:16])=[C:14]([CH3:15])[C:8]=2[O:7]1

Participants

Conditions

Temperature: 120 °C

Procedure

To a solution of DMSO (12 mL) containing 1-(2,2,4,6,7-pentamethyl-2,3-dihydro-1-benzofuran-5-yl)piperazine (1.1 g, 4.00 mmol) synthesized in Reference Example 61, 2-bromopyrimidine (954 mg, 6.0 mmol) and diisopropylethylamine (2.09 mL) were added, and the mixture was stirred at 120° C. for 2 hours. The reaction solution was diluted with ethyl acetate, and washed with water and saturated saline. The organic layer was dried using magnesium sulfate. The solvent was removed under reduced pressure, and the obtained residue was purified by silica gel column chromatography (hexane-ethyl acetate 9:1). The obtained solid was recrystallized from ethanol-water to obtain 600 mg of the title compound (yield 42%).

Workup

additionwere added
washwashed with water and saturated saline
customThe organic layer was dried
customThe solvent was removed under reduced pressure
customthe obtained residue was purified by silica gel column chromatography (hexane-ethyl acetate 9:1)
customThe obtained solid was recrystallized from ethanol-water

Sources & evidence

ORD record: ord-4b61e97cd7ae4f1db592868105ee867e
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08957069B2

Reaction notes

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