Cesium carbonate → 3-[(6-[3-(1-Methylimidazolin-2-yl)phenoxy]-2-phenylpyrimidin-4-yl)oxy]-4-(benzyloxy)benzonitrile

HRID 841982

Reaction equation

Cl[C:2]1[N:7]=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[N:5]=[C:4]([O:14][C:15]2[CH:16]=[C:17]([CH:20]=[CH:21][C:22]=2[O:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C:18]#[N:19])[CH:3]=1.C([O-])([O-])=O.[Cs+].[Cs+].[OH:37][C:38]1[CH:39]=[C:40]([C:44]2[N:45]([CH3:49])[CH2:46][CH2:47][N:48]=2)[CH:41]=[CH:42][CH:43]=1>CS(C)=O>[CH3:49][N:45]1[CH2:46][CH2:47][N:48]=[C:44]1[C:40]1[CH:39]=[C:38]([CH:43]=[CH:42][CH:41]=1)[O:37][C:2]1[N:7]=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[N:5]=[C:4]([O:14][C:15]2[CH:16]=[C:17]([CH:20]=[CH:21][C:22]=2[O:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C:18]#[N:19])[CH:3]=1

Participants

Conditions

Temperature: 50 °C

Procedure

To 3-[(6-chloro-2-phenylpyrimidin-4-yl)oxy]-4-(benzyloxy)benzonitrile (1.0 g, 2.4 mmol) in DMSO (12 mL) was added Cs2CO3 (0.8 g, 2.5 mmol) and 2-(3-hydroxyphenyl)-1-methylimidazoline (0.44 g, 2.5 mmol). After stirring in an oil bath at 50° C. for 24 hours, the reaction was partitioned with water and ethyl acetate. The layers were separated, washed with water and brine, dried (Na2SO4), and the solvent was removed in vacuo. The residue was chromatographed on silica gel with CH2CL2/MeOH/NH4OH (120/5/1) to give 0.5 g of 3-[(6-[3-(1-methylimidazolin-2-yl)phenoxy]-2-phenylpyrimidin-4-yl)oxy]-4-(benzyloxy)benzonitrile.

Workup

customthe reaction was partitioned with water and ethyl acetate
customThe layers were separated
washwashed with water and brine
dry with materialdried (Na2SO4)
customthe solvent was removed in vacuo
customThe residue was chromatographed on silica gel with CH2CL2/MeOH/NH4OH (120/5/1)

Sources & evidence

ORD record: ord-84f7323fa3c74497ac86cfde93961eea
Source dataset: uspto-grants-2002_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06372751B1

Linked notes

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