Potassium Carbonate → HCID 178429475, compound

HRID 630128Notes

Reaction equation

HRID 630128 reaction equation
Cl.Cl[CH2:3][C:4]1[N:8]([CH:9]([CH3:11])[CH3:10])[CH:7]=[N:6][C:5]=1[CH3:12].[CH3:13][C:14]1[N:19]=[C:18]([SH:20])[N:17]=[C:16]([OH:21])[CH:15]=1.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH3:13][C:14]1[N:19]=[C:18]([S:20][CH2:3][C:4]2[N:8]([CH:9]([CH3:11])[CH3:10])[CH:7]=[N:6][C:5]=2[CH3:12])[N:17]=[C:16]([OH:21])[CH:15]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 668208845-(chloromethyl)-4-methyl-1-(propan-2-yl)-1H-imidazole hydrochlorideHCID 178429541HCID 178429541, compound

Product 1

HCID 178429475HCID 178429475, compoundYield 28%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 5-(chloromethyl)-4-methyl-1-(propan-2-yl)-1H-imidazole hydrochloride (824 g, 3.9 mmol), 6-methyl-2-sulfanylpyrimidin-4-ol (970 mg, 7.0 mmol), and potassium carbonate (1.2 g, 9.0 mmol) in acetone (30 mL) was stirred at room temperature for 2 days. The solid material was removed by filtration. The filtrate was recovered and evaporated. The crude product was purified by flash chromatography (0-8% MeOH/DCM), affording 6-methyl-2-({[4-methyl-1-(propan-2-yl)-1H-imidazol-5-yl]methyl}-sulfanyl)pyrimidin-4-ol (215 mg, 28% yield); 1H NMR (400 MHz, DMSO-d6): δ 1.36 (d, 3H, J=6.7 Hz), 2.09 (s, 3H), 2.19 (s, 3H), 4.31 (m, 1H), 4.45 (s, 2H), 6.00 (s, 1H), 7.66 (s, 1H); M+279. 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 (0-8% MeOH/DCM)

Sources & evidence

ORD record
ord-12abb2b0a576453e94bcafef038ad810
Source dataset
uspto-grants-2016_04
Patent number
US09315521B2

Reaction notes

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