Phenol → [2,6-Dimethyl-4-(5-phenoxy-oxazolo[5,4-d]pyrimidin-2-yl)-phenoxy]-acetic acid tert-butyl ester

HRID 81384Notes

Reaction equation

HRID 81384 reaction equation
[H-].[Na+].[C:3]1([OH:9])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[C:10]([O:14][C:15](=[O:36])[CH2:16][O:17][C:18]1[C:23]([CH3:24])=[CH:22][C:21]([C:25]2[O:26][C:27]3[N:28]=[C:29](Cl)[N:30]=[CH:31][C:32]=3[N:33]=2)=[CH:20][C:19]=1[CH3:35])([CH3:13])([CH3:12])[CH3:11]>CC(N(C)C)=O>[C:10]([O:14][C:15](=[O:36])[CH2:16][O:17][C:18]1[C:23]([CH3:24])=[CH:22][C:21]([C:25]2[O:26][C:27]3[N:28]=[C:29]([O:9][C:3]4[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=4)[N:30]=[CH:31][C:32]=3[N:33]=2)=[CH:20][C:19]=1[CH3:35])([CH3:13])([CH3:12])[CH3:11]

Participants

5

Reactant 3

HCID 996PhenolHCID 24758Sodium hydrideHCID 86679893[4-(5-Chloro-oxazolo[5,4-d]pyrimidin-2-yl)-2,6-dimethyl-phenoxy]-acetic acid tert-butyl ester

Product 1

HCID 86679894[2,6-Dimethyl-4-(5-phenoxy-oxazolo[5,4-d]pyrimidin-2-yl)-phenoxy]-acetic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent2×

Procedure

19 mg of sodium hydride were added under an argon atmosphere to a solution of 38 mg of phenol in 5 ml of dimethylacetamide. After stirring for 30 min at room temperature, a solution of 156 mg of [4-(5-chloro-oxazolo[5,4-d]pyrimidin-2-yl)-2,6-dimethyl-phenoxy]-acetic acid tert-butyl ester in 3 ml of dimethylacetamide was added slowly. The mixture was allowed to stir for 1.5 h at room temperature. Upon consumption of the starting ester an aqueous solution of citric acid (100 g/l) was added until the pH was neutral. The aqueous layer was extracted twice with 15 ml ethyl acetate. The combined organic layers were dried over sodium sulfate, filtered and the solvents were removed in vacuo. The title compound was isolated by silica gel chromatography (heptane/ethyl acetate gradient). Yield: 77 mg of a white solid.

Workup

  1. stirringto stir for 1.5 h at room temperature
  2. customUpon consumption of the starting ester an aqueous solution of citric acid (100 g/l)
  3. additionwas added until the pH
  4. extractionThe aqueous layer was extracted twice with 15 ml ethyl acetate
  5. dry with materialThe combined organic layers were dried over sodium sulfate
  6. filtrationfiltered
  7. customthe solvents were removed in vacuo

Sources & evidence

ORD record
ord-5894b2320fdc46bc8dee19f753a981e8
Source dataset
uspto-grants-2014_09
Patent number
US08846692B2

Reaction notes

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