Water → HCID 70807105, compound

HRID 880092Notes

Reaction equation

HRID 880092 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

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 20975526HCID 20975526, compoundHCID 68099727HCID 68099727, compound

Product 1

HCID 70807105HCID 70807105, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

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

  1. stirringthe resulting mixture is stirred at ambient temperature overnight
  2. concentrationthe reaction mixture is concentrated to dryness under reduced pressure
  3. customAfter purification
  4. washby silica column chromatography, elution

Sources & evidence

ORD record
ord-69b2669d02bd41639c4c2ebd497730fb
Source dataset
uspto-grants-2015_03
Patent number
US08993565B2

Reaction notes

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