Potassium Carbonate → {4-[5-(2-Fluoro-phenoxy)-oxazolo[5,4-d]pyrimidin-2-yl]-2,6-dimethyl-phenoxy}-acetic acid

HRID 81361Notes

Reaction equation

[F:1][C:2]1[CH:26]=[CH:25][CH:24]=[CH:23][C:3]=1[O:4][C:5]1[N:6]=[CH:7][C:8]2[N:13]=[C:12]([C:14]3[CH:19]=[C:18]([CH3:20])[C:17]([OH:21])=[C:16]([CH3:22])[CH:15]=3)[O:11][C:9]=2[N:10]=1.Br[CH2:28][C:29]([O:31]C(C)(C)C)=[O:30].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[F:1][C:2]1[CH:26]=[CH:25][CH:24]=[CH:23][C:3]=1[O:4][C:5]1[N:6]=[CH:7][C:8]2[N:13]=[C:12]([C:14]3[CH:15]=[C:16]([CH3:22])[C:17]([O:21][CH2:28][C:29]([OH:31])=[O:30])=[C:18]([CH3:20])[CH:19]=3)[O:11][C:9]=2[N:10]=1

Participants

Conditions

Temperature: 60 °C

Procedure

A suspension of 430 mg of 4-[5-(2-fluoro-phenoxy)-oxazolo[5,4-d]pyrimidin-2-yl]-2,6-dimethyl-phenol, 0.2 ml of tert-butyl bromoacetate and 423 of mg potassium carbonate in 5 ml of dimethylformamide was stirred at 60° C. for 2 h. After cooling, the solids were removed by filtration and the solvent were distilled off in vacuo. 1.3 ml of trifluoroacetic acid were added to the residue, and the solution was stirred at room temperature for 1 h. Then 10 ml of toluene were added and the solvents were removed in vacuo. The title compound was isolated by silica gel chromatography (heptane/ethyl acetate gradient) as a white solid (135 mg).

Workup

temperatureAfter cooling
customthe solids were removed by filtration
distillationthe solvent were distilled off in vacuo
addition1.3 ml of trifluoroacetic acid were added to the residue
stirringthe solution was stirred at room temperature for 1 h
additionThen 10 ml of toluene were added
customthe solvents were removed in vacuo

Sources & evidence

ORD record: ord-f4e39e7fc0fd469aaeaed200d4e5014a
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08846690B2

Reaction notes

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