Cesium carbonate → 7-(2,5-Dichloro-pyrimidin-4-yloxy)-2-methyl-2,3-dihydro-isoindol-1-one

HRID 81354

Reaction equation

[Cl:1][C:2]1[N:7]=[C:6](Cl)[C:5]([Cl:9])=[CH:4][N:3]=1.[OH:10][C:11]1[CH:12]=[CH:13][CH:14]=[C:15]2[C:19]=1[C:18](=[O:20])[N:17]([CH3:21])[CH2:16]2.C(=O)([O-])[O-].[Cs+].[Cs+]>C(Cl)Cl>[Cl:1][C:2]1[N:7]=[C:6]([O:10][C:11]2[CH:12]=[CH:13][CH:14]=[C:15]3[C:19]=2[C:18](=[O:20])[N:17]([CH3:21])[CH2:16]3)[C:5]([Cl:9])=[CH:4][N:3]=1

Participants

Conditions

Temperature: 0 °C

Procedure

2,4,5-trichloropyrimidine (0.20 g) and 7-hydroxy-2-methyl-2,3-dihydro-isoindol-1-one are dissolved in DCM (10 mL), cooled to 0° C. and combined with caesium carbonate (0.75 g). The cooling bath is removed and the mixture is stirred for 16 h. For working up the mixture is combined with 10% NaCl solution (100 mL) and extracted three times with 75 mL ethyl acetate. The combined organic phases are dried on magnesium sulphate, filtered off from the desiccant and the solvent is eliminated in vacuo.

Workup

customThe cooling bath is removed
extractionextracted three times with 75 mL ethyl acetate
customThe combined organic phases are dried on magnesium sulphate
filtrationfiltered off from the desiccant and the solvent

Sources & evidence

ORD record: ord-434867972c824e36b147a39657cc7d76
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08846689B2

Linked notes

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