Water → HCID 70807105, compound
Reaction equation
[H-].[Na+].[CH3:3][C:4]([O:7][C:8]([O:10][C:11]1[CH:16]=[C:15]([N:17]2[CH2:22][CH2:21][O:20][CH2:19][CH2:18]2)[N:14]=[C:13]([CH2:23][C:24]([O:26][CH2:27][CH3:28])=[O:25])[N:12]=1)=[O:9])([CH3:6])[CH3:5].[I-].[CH4:30].O>CN(C)C=O>[CH3:6][C:4]([O:7][C:8]([O:10][C:11]1[CH:16]=[C:15]([N:17]2[CH2:18][CH2:19][O:20][CH2:21][CH2:22]2)[N:14]=[C:13]([CH:23]([CH3:30])[C:24]([O:26][CH2:27][CH3:28])=[O:25])[N:12]=1)=[O:9])([CH3:3])[CH3:5]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
84 mg of sodium hydride are added to a solution of 700 mg of ethyl [4-({[(2-methylpropan-2-yl)oxy]carbonyl}oxy)-6-(morpholin-4-yl)pyrimidin-2-yl]acetate in 8 ml of N,N-dimethylformamide under argon. The reaction mixture is then stirred for 15 minutes at 0° C. 0.130 ml of methane iodide is then added and the resulting mixture is stirred at ambient temperature overnight. 0.5 ml of water is added and the reaction mixture is concentrated to dryness under reduced pressure. After purification by silica column chromatography, elution being carried out with a gradient of heptane/ethyl acetate eluent of 0% to 50% and then with ethyl acetate at 100%. 150 mg of ethyl 2-[4-({[(2-methylpropan-2-yl)oxy]carbonyl}oxy)-6-(morpholin-4-yl)pyrimidin-2-yl]propanoate are obtained in the form of a colourless oil.
Workup
- stirringthe resulting mixture is stirred at ambient temperature overnight
- concentrationthe reaction mixture is concentrated to dryness under reduced pressure
- customAfter purification
- washby silica column chromatography, elution
Sources & evidence
- ORD record
- ord-58f0efedb31e4b5e962d8827784212a1
- Source dataset
- uspto-grants-2014_07
- Patent number
- US08791255B2
Reaction notes
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