Water → HCID 136163974, compound

HRID 1487433Notes

Reaction equation

HRID 1487433 reaction equation
[OH:1][CH2:2][C:3]1[C:4]([C:11]2[NH:12][CH:13]=[CH:14][N:15]=2)=[C:5]([OH:10])[C:6]([CH3:9])=[N:7][CH:8]=1.CI.[C:18]([O-])([O-])=O.[K+].[K+].O>CN(C=O)C>[OH:1][CH2:2][C:3]1[C:4]([C:11]2[N:15]([CH3:18])[CH:14]=[CH:13][N:12]=2)=[C:5]([OH:10])[C:6]([CH3:9])=[N:7][CH:8]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodide2×HCID 11430Potassium CarbonateHCID 135532669667398-46-1

Product 1

HCID 136163974HCID 136163974, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

5-(hydroxymethyl)-4-(1H-imidazol-2-yl)-2-methylpyridin-3-ol (1.03 g, 5.0 mmol) was suspended in DMF (50 mL) and methyl iodide (0.31 mL, 5 mmol) was added at rt. The reaction mixture was stirred over a period of 19 h and a further portion of methyl iodide (0.125 mL, 2 mmol) was added and stirred over a period of 23 h. Aq. K2CO3 solution (10 mL) and water (50 mL) was added and extracted with ethyl acetate (2×50 mL). Combined organic layers were dried over MgSO4 (10 g) and evaporated to a volume of 20 mL. After 3 days at room temperature, the crystallized product was filtered off and dried to give (600 mg) the title compound as a light beige solid.

Workup

  1. stirringstirred over a period of 23 h
  2. extractionextracted with ethyl acetate (2×50 mL)
  3. dry with materialCombined organic layers were dried over MgSO4 (10 g)
  4. customevaporated to a volume of 20 mL
  5. waitAfter 3 days at room temperature
  6. filtrationthe crystallized product was filtered off
  7. customdried

Sources & evidence

ORD record
ord-3c160a64e43542dea37748f9fb967dcc
Source dataset
uspto-grants-2016_08
Patent number
US09428533B2

Reaction notes

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