Methyl iodide → HCID 56960510, compound

HRID 1626354Notes

Reaction equation

HRID 1626354 reaction equation
[O:1]=[C:2]1[NH:6][C:5](=[O:7])/[C:4](=[CH:8]/[C:9]2[CH:10]=[C:11]([CH:32]=[CH:33][CH:34]=2)[O:12][C:13]2[N:18]=[CH:17][N:16]=[C:15]([O:19][CH:20]3[CH2:25][CH2:24][N:23]([C:26]([O:28][CH2:29][CH3:30])=[O:27])[CH2:22][CH2:21]3)[C:14]=2[CH3:31])/[S:3]1.[C:35]([O-])([O-])=O.[K+].[K+].CI>CC(N(C)C)=O>[CH2:29]([O:28][C:26]([N:23]1[CH2:24][CH2:25][CH:20]([O:19][C:15]2[C:14]([CH3:31])=[C:13]([O:12][C:11]3[CH:32]=[CH:33][CH:34]=[C:9](/[CH:8]=[C:4]4/[C:5](=[O:7])[N:6]([CH3:35])[C:2](=[O:1])[S:3]/4)[CH:10]=3)[N:18]=[CH:17][N:16]=2)[CH2:21][CH2:22]1)=[O:27])[CH3:30]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 118249754HCID 118249754, compound

Product 1

HCID 56960510HCID 56960510, compoundYield 97.1%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
27 °C

Procedure

To a solution (Z)-ethyl 4-((6-(3-((2,4-dioxothiazolidin-5-ylidene)methyl)phenoxy)-5-methylpyrimidin-4-yl)oxy)piperidine-1-carboxylate (300 mg, 0.0006198 mole) in dimethyl acetamide (10 ml), K2CO3 (171 mg, 0.001239 mole) was added followed by addition of methyl iodide (0.060 ml, 0.0009297 mole) at 0° C. and reaction mixture was stirred at 27° C. for 30 minutes. Then reaction mixture was poured into ice cold water and extracted with ethyl acetate. Organic layer was washed with water and brine, dried over sodium sulfate and evaporated on a rotavpour to yield the product as yellow solid (300 mg).

Workup

  1. customreaction mixture
  2. customThen reaction mixture
  3. additionwas poured into ice cold water
  4. extractionextracted with ethyl acetate
  5. washOrganic layer was washed with water and brine
  6. dry with materialdried over sodium sulfate
  7. customevaporated on a rotavpour

Sources & evidence

ORD record
ord-2676d09d4b74401daa3162514a4e2f41
Source dataset
uspto-grants-2014_07
Patent number
US08785463B2

Reaction notes

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