Potassium Carbonate → tert-Butyl[4-(7-chloro-5-methylsulfanyloxazolo[5,4-d]pyrimidin-2-yl)-2,6-dimethylphenoxy]acetate

HRID 633616Notes

Reaction equation

C(=O)([O-])[O-].[K+].[K+].[Cl:7][C:8]1[C:9]2[N:18]=[C:17]([C:19]3[CH:24]=[C:23]([CH3:25])[C:22]([OH:26])=[C:21]([CH3:27])[CH:20]=3)[O:16][C:10]=2[N:11]=[C:12]([S:14][CH3:15])[N:13]=1.Br[CH2:29][C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31]>CN(C)C=O>[Cl:7][C:8]1[C:9]2[N:18]=[C:17]([C:19]3[CH:24]=[C:23]([CH3:25])[C:22]([O:26][CH2:29][C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])=[C:21]([CH3:27])[CH:20]=3)[O:16][C:10]=2[N:11]=[C:12]([S:14][CH3:15])[N:13]=1

Participants

Conditions

Temperature: 60 °C

Procedure

7.46 g of potassium carbonate were added to a solution of 4.34 g of 4-(7-chloro-5-methylsulfanyloxazolo[5,4-d]pyrimidin-2-yl)-2,6-dimethylphenol in 45 ml of dimethylformamide, and 2.90 g of tert-butyl bromoacetate were then added. The mixture was stirred at 60° C. for 1 h. The cooled reaction mixture was then added to ice water, and the precipitated solid was filtered off with suction and washed with water. The solid was taken up in dichloromethane and dried over sodium sulfate, activated carbon was added and the mixture was filtered and concentrated under reduced pressure. This gave 4.20 g (71%) of the title compound, which was reacted further without any further purification.

Workup

additionwere then added
customThe cooled reaction mixture
filtrationthe precipitated solid was filtered off with suction
washwashed with water
dry with materialdried over sodium sulfate, activated carbon
additionwas added
filtrationthe mixture was filtered
concentrationconcentrated under reduced pressure
customThis gave 4.20 g (71%) of the title compound, which was reacted further without any further purification

Sources & evidence

ORD record: ord-13169866d1014eb9a6548b35d9ea6f12
Source dataset: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09321787B2

Reaction notes

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