Methyl iodide → HCID 86698488, compound

HRID 403406Notes

Reaction equation

HRID 403406 reaction equation
[H-].[Na+].[C:3]([O:7][C:8](=[O:23])[NH:9][C:10]1[C:11]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[CH3:22])=[N:12][CH:13]=[N:14][CH:15]=1)([CH3:6])([CH3:5])[CH3:4].IC.[C:26](=O)(O)[O-].[Na+]>O1CCCC1>[C:3]([O:7][C:8](=[O:23])[N:9]([CH3:26])[C:10]1[C:11]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[CH3:22])=[N:12][CH:13]=[N:14][CH:15]=1)([CH3:6])([CH3:5])[CH3:4]

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 516892Sodium BicarbonateHCID 86698489HCID 86698489, compound

Product 1

HCID 86698488HCID 86698488, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Sodium hydride (75 mg, 1.87 mmol) was added to a stirring solution of (4-o-tolyl-pyrimidin-5-yl)-carbamic acid tert-butyl ester (410 mmol, 1.44 mmol) in tetrahydrofuran (10 mL) under Argon atmosphere. After 10 min., iodomethane (117 μL, 1.87 mmol) was added. The reaction mixture was stirred for 16 hours and then poured into saturated aqueous sodium bicarbonate solution and extracted three times with ethyl acetate. The combined organic layers were washed with brine and dried over magnesium sulfate. Filtration followed by removal of volatiles gave the crude product. Flash chromatography on silica gel (33% ethyl acetate in n-hexane) gave the product as a yellow solid (242 mg, 56%) which was pure enough for the next step.

Workup

  1. extractionextracted three times with ethyl acetate
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationFiltration
  5. customfollowed by removal of volatiles
  6. customgave the crude product

Sources & evidence

ORD record
ord-977c9d9623624526826f85fb10fac194
Source dataset
uspto-grants-2014_06
Patent number
US08748434B2

Reaction notes

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