Potassium Carbonate → [4-(5-Chloro-oxazolo[5,4-d]pyrimidin-2-yl)-2,6-dimethyl-phenoxy]-acetic acid tert-butyl ester

HRID 81383Notes

Reaction equation

HRID 81383 reaction equation
[Cl:1][C:2]1[N:3]=[CH:4][C:5]2[N:10]=[C:9]([C:11]3[CH:16]=[C:15]([CH3:17])[C:14]([OH:18])=[C:13]([CH3:19])[CH:12]=3)[O:8][C:6]=2[N:7]=1.Br[CH2:21][C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[C:25]([O:24][C:22](=[O:23])[CH2:21][O:18][C:14]1[C:13]([CH3:19])=[CH:12][C:11]([C:9]2[O:8][C:6]3[N:7]=[C:2]([Cl:1])[N:3]=[CH:4][C:5]=3[N:10]=2)=[CH:16][C:15]=1[CH3:17])([CH3:28])([CH3:27])[CH3:26]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 79177tert-Butyl bromoacetateHCID 1363977474-(5-Chlorooxazolo[5,4-d]pyrimidin-2-yl)-2,6-dimethylphenol

Product 1

HCID 86679893[4-(5-Chloro-oxazolo[5,4-d]pyrimidin-2-yl)-2,6-dimethyl-phenoxy]-acetic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of 1 g of 4-(5-chloro-oxazolo[5,4-d]pyrimidin-2-yl)-2,6-dimethyl-phenol in 5 ml of dimethylformamide was added slowly to a suspension of 1.2 ml of tert-butyl bromoacetate and 1.3 g of potassium carbonate in 15 ml of dimethylformamide. The mixture was stirred at room temperature for 30 min and then heated to 50° C. for 4 h. After cooling, the solids were removed by filtration and the solvents were distilled off in vacuo to give 1.4 g of the crude title compound as a pale yellow solid.

Workup

  1. temperatureheated to 50° C. for 4 h
  2. temperatureAfter cooling
  3. customthe solids were removed by filtration
  4. distillationthe solvents were distilled off in vacuo

Sources & evidence

ORD record
ord-636f1623e81046ffb47ed0f7841cec59
Source dataset
uspto-grants-2014_09
Patent number
US08846692B2

Reaction notes

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