Potassium Carbonate → HCID 178462642, compound

HRID 577007Notes

Reaction equation

HRID 577007 reaction equation
[Cl-].Cl[CH2:3][C:4]1[NH+:5]([CH2:9][CH3:10])[CH:6]=[CH:7][N:8]=1.[CH3:11][C:12]1[N:17]=[C:16]([SH:18])[N:15]=[C:14]([OH:19])[CH:13]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH2:9]([N:5]1[CH:6]=[CH:7][N:8]=[C:4]1[CH2:3][S:18][C:16]1[N:15]=[C:14]([OH:19])[CH:13]=[C:12]([CH3:11])[N:17]=1)[CH3:10]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 66820805135206-88-1HCID 178429541HCID 178429541, compound

Product 1

HCID 178462642HCID 178462642, compoundYield 21.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 2-(chloromethyl)-1-ethyl-1H-imidazol-1-ium chloride (1.0 g, 5.5 mmol), 6-methyl-2-sulfanylpyrimidin-4-ol (650 mg, 4.6 mmol), and potassium carbonate (2.0 g, 14.4 mmol) in anhydrous DMF (10 mL) was stirred at room temperature overnight. The reaction mixture was evaporated under reduced pressure. The solid residue was treated with dichloromethane (20 mL) and brine (60 mL). The aqueous layer was recovered and evaporated. The residue was purified by flash chromatography (0-20% MeOH/CH2Cl2), affording 2-{[(1-ethyl-1H-imidazol-2-yl)methyl]sulfanyl}-6-methylpyrimidin-4-ol (244 mg, 21% yield); 1H NMR (400 MHz, DMSO-d6): δ 1.27 (t, 3H, J=7.2 Hz), 2.17 (s, 3H), 4.00 (m, 2H), 4.50 (s, 2H), 6.00 (s, 1H), 6.81 (s, 1H), 7.15 (s, 1H); M+ 251. The product was used without further purification.

Workup

  1. customThe reaction mixture was evaporated under reduced pressure
  2. additionThe solid residue was treated with dichloromethane (20 mL) and brine (60 mL)
  3. customThe aqueous layer was recovered
  4. customevaporated
  5. customThe residue was purified by flash chromatography (0-20% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-51b3c359ac6a46f8b2691e8b90e73299
Source dataset
uspto-grants-2015_05
Patent number
US09040538B2

Reaction notes

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