Potassium Carbonate → HCID 178462825, compound

HRID 577081Notes

Reaction equation

HRID 577081 reaction equation
Cl.Cl[CH2:3][C:4]1[N:5]=[CH:6][N:7]([CH2:10][CH3:11])[C:8]=1[CH3:9].[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>[CH2:10]([N:7]1[C:8]([CH3:9])=[C:4]([CH2:3][S:19][C:17]2[N:16]=[C:15]([OH:20])[CH:14]=[C:13]([CH3:12])[N:18]=2)[N:5]=[CH:6]1)[CH3:11]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 668207564-(chloromethyl)-1-ethyl-5-methyl-1H-imidazole hydrochlorideHCID 178429541HCID 178429541, compound

Product 1

HCID 178462825HCID 178462825, compoundYield 32.3%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 4-(chloromethyl)-1-ethyl-5-methyl-1H-imidazole hydrochloride (450 mg, 2.3 mmol), 6-methyl-2-sulfanylpyrimidin-4-ol (215 mg, 1.5 mmol), and potassium carbonate (720 mg, 5.2 mmol) in acetone (15 mL) was stirred at room temperature for 3 days. 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-5-methyl-1H-imidazol-4-yl)methyl]sulfanyl}-6-methylpyrimidin-4-ol (128 mg, 32% yield); 1H NMR (400 MHz, DMSO-d6): δ 1.26 (t, 3H, J=6.7 Hz), 2.18 (m, 6H), 3.86 (m, 2H), 4.26 (s, 2H), 5.95 (s, 1H), 7.55 (s, 11-1); 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-5a89ca89b1064de29b05390870b0459c
Source dataset
uspto-grants-2015_05
Patent number
US09040538B2

Reaction notes

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