Potassium Carbonate → HCID 178429465, compound

HRID 577118Notes

Reaction equation

HRID 577118 reaction equation
Br[CH2:2][C:3]1[N:7]([CH3:8])[CH:6]=[N:5][C:4]=1[Cl:9].C(=O)([O-])[O-].[K+].[K+].[CH3:16][C:17]1[N:22]=[C:21]([SH:23])[N:20]=[C:19]([OH:24])[CH:18]=1>CN(C=O)C>[Cl:9][C:4]1[N:5]=[CH:6][N:7]([CH3:8])[C:3]=1[CH2:2][S:23][C:21]1[N:20]=[C:19]([OH:24])[CH:18]=[C:17]([CH3:16])[N:22]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 595893705-(bromomethyl)-4-chloro-1-methyl-1H-imidazoleHCID 178429541HCID 178429541, compound

Product 1

HCID 178429465HCID 178429465, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

5-(bromomethyl)-4-chloro-1-methyl-1H-imidazole was dissolved in DMF (20 mL). Potassium carbonate (3 g) and 6-methyl-2-sulfanylpyrimidin-4-ol (1.4 g, 10 mmol) were added. The new mixture was stirred at room temperature for 2 hours. DMF was removed under vacuum. The crude compound was purified by column chromatography to provide 2-{[(4-chloro-1-methyl-1H-imidazol-5-yl)methyl]sulfanyl}-6-methylpyrimidin-4-ol as the major product (350 mg, 13% overall yield); 1H NMR (400 MHz, DMSO-d6): δ 2.19 (s, 3H), 3.72 (s, 3H), 4.59 (s, 2H), 6.00 (bs, 1H), 7.59 (s, 1H); M+ 271.

Workup

  1. customDMF was removed under vacuum
  2. customThe crude compound was purified by column chromatography

Sources & evidence

ORD record
ord-340b72e55299477188c307d9a0d295ed
Source dataset
uspto-grants-2015_05
Patent number
US09040538B2

Reaction notes

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