Dimethylformamide → HCID 15070275, compound

HRID 1073025Notes

Reaction equation

[OH:1][CH:2]([C:7]([CH3:10])([CH3:9])[CH3:8])[C:3]([O:5][CH3:6])=[O:4].[CH3:11][C:12]1[CH:17]=[C:16]([CH3:18])[N:15]=[C:14](S(C)(=O)=O)[N:13]=1.C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>O>[CH3:11][C:12]1[CH:17]=[C:16]([CH3:18])[N:15]=[C:14]([O:1][CH:2]([C:7]([CH3:10])([CH3:9])[CH3:8])[C:3]([O:5][CH3:6])=[O:4])[N:13]=1

Participants

Conditions

Temperature: 100 °C

Procedure

2.9 g of methyl 2-hydroxy-3,3-dimethybutyrate, 4.1 g of 4,6 -dimethyl-2-methylsulfonylpyrimidine and 3.3 g of potassium carbonate were added to 50 ml of N,N-dimethylformamide, and the mixture was stirred at 100° C. for 4 hours. The reaction solution was cooled to room temperature, poured into water and extracted with 100 ml of ethyl acetate. The organic layer was washed twice with a sodium chloride aqueous solution, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The liquid substance thereby obtained was purified by silica gel column chromatography (eluent: hexane/ethyl acetate =6/1) to obtain 4.2 g of the desired product.

Workup

temperatureThe reaction solution was cooled to room temperature
extractionextracted with 100 ml of ethyl acetate
washThe organic layer was washed twice with a sodium chloride aqueous solution
dry with materialdried over anhydrous sodium sulfate
concentrationconcentrated under reduced pressure
customThe liquid substance thereby obtained
customwas purified by silica gel column chromatography (eluent: hexane/ethyl acetate =6/1)

Sources & evidence

ORD record: ord-93c1f599379a44d6846451f41d515ed7
Source dataset: uspto-grants-1990_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04968340

Reaction notes

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