Potassium Carbonate → HCID 178462642, compound

HRID 630048Notes

Reaction equation

HRID 630048 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-ded39b78790542329f0840fb6e5034c1
Source dataset
uspto-grants-2016_04
Patent number
US09315521B2

Reaction notes

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