Methyl iodide → HCID 22599805, compound

HRID 1759970Notes

Reaction equation

HRID 1759970 reaction equation
[H-].[Na+].[CH3:3][S:4][C:5]1[N:10]=[CH:9][N:8]=[C:7]([CH:11]([OH:18])[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:6]=1.I[CH3:20].[Cl-].[NH4+]>O1CCCC1>[CH3:3][S:4][C:5]1[N:10]=[CH:9][N:8]=[C:7]([CH:11]([O:18][CH3:20])[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:6]=1

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 22599669HCID 22599669, compound

Product 1

HCID 22599805HCID 22599805, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

In 3 ml of tetrahydrofuran was suspended 0.08 g of sodium hydride (60% in oil), to which 6-methylthio-4-(α-hydroxylbenzyl)pyrimidine dissolved in 0.3 ml of tetrahydrofuran was added. The mixture was stirred at 0° C. for 15 minutes, to which 0.28 g of iodomethane was added dropwise at room temperature, followed by stirring at the same temperature for 30 minutes. The reaction mixture was then poured into a saturated aqueous ammonium chloride solution and extracted three times with ethyl acetate. The organic layers were combined, washed with water, dried over anhydrous magnesium sulfate, and then concentrated. The residue was subjected to silica gel column chromatography to give 0.17 g of 6-methylthio-4-(α-methoxybenzyl)pyrimidine.

Workup

  1. additionwas added
  2. additionwas added dropwise at room temperature
  3. extractionextracted three times with ethyl acetate
  4. washwashed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-2686dc7358f3402d8641adde9ca7fac7
Source dataset
uspto-grants-2005_01
Patent number
US06838463B2

Reaction notes

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