Potassium Carbonate → HCID 178462821, compound

HRID 577076Notes

Reaction equation

HRID 577076 reaction equation
Cl.Cl[CH2:3][C:4]1[N:8]([CH2:9][CH3:10])[CH:7]=[N:6][C:5]=1[CH3:11].[CH3:12][C:13]1[N:18]=[C:17]([SH:19])[N:16]=[C:15]([OH:20])[CH:14]=1.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH2:9]([N:8]1[C:4]([CH2:3][S:19][C:17]2[N:16]=[C:15]([OH:20])[CH:14]=[C:13]([CH3:12])[N:18]=2)=[C:5]([CH3:11])[N:6]=[CH:7]1)[CH3:10]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 668206265-(chloromethyl)-1-ethyl-4-methyl-1H-imidazole hydrochlorideHCID 178429541HCID 178429541, compound

Product 1

HCID 178462821HCID 178462821, compoundYield 46.3%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 5-(chloromethyl)-1-ethyl-4-methyl-1H-imidazole hydrochloride (1.0 g, 5.1 mmol), 6-methyl-2-sulfanylpyrimidin-4-ol (500 mg, 3.5 mmol), and potassium carbonate (1.2 g, 9.0 mmol) in acetone (25 mL) was stirred at room temperature overnight. The solid material was removed by filtration. The filtrate was recovered and evaporated. The crude product was purified by flash chromatography (0-6% MeOH/DCM), affording 2-{[(1-ethyl-4-methyl-1H-imidazol-5-yl)methyl]sulfanyl}-6-methyl-pyrimidin-4-ol (428 mg, 46% yield); 1H NMR (400 MHz, DMSO-d6): δ 1.31 (t, 3H, J=6.7 Hz), 2.11 (s, 3H), 2.22 (s, 3H), 3.95 (m, 2H), 4.48 (s, 2H), 6.02 (s, 1H), 7.54 (s, 1H); M+ 266. The product was used without further purification.

Workup

  1. customThe solid material was removed by filtration
  2. customThe filtrate was recovered
  3. customevaporated
  4. customThe crude product was purified by flash chromatography (0-6% MeOH/DCM)

Sources & evidence

ORD record
ord-b1a1af0f74ee4390b01164fcecc5f900
Source dataset
uspto-grants-2015_05
Patent number
US09040538B2

Reaction notes

Loading…