Potassium Carbonate → HCID 178429464, compound

HRID 630165Notes

Reaction equation

HRID 630165 reaction equation
[Cl:1][C:2]1[N:3]([CH:10]([CH3:12])[CH3:11])[C:4]([CH2:8]O)=[C:5]([Cl:7])[N:6]=1.P(Br)(Br)Br.C(=O)([O-])[O-].[K+].[K+].[CH3:23][C:24]1[N:29]=[C:28]([SH:30])[N:27]=[C:26]([OH:31])[CH:25]=1>C(Cl)(Cl)Cl>[Cl:1][C:2]1[N:3]([CH:10]([CH3:12])[CH3:11])[C:4]([CH2:8][S:30][C:28]2[N:27]=[C:26]([OH:31])[CH:25]=[C:24]([CH3:23])[N:29]=2)=[C:5]([Cl:7])[N:6]=1

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 24614Phosphorus tribromideHCID 59589460HCID 59589460, compoundHCID 178429541HCID 178429541, compound

Product 1

HCID 178429464HCID 178429464, compoundYield 21%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

[2,4-dichloro-1-(propan-2-yl)-1H-imidazol-5-yl]methanol was dissolved in chloroform (40 mL), followed by addition of PBr3 (1.9 mL, 20 mmol). The resulting mixture was stirred at room temperature overnight. The solvent was evaporated and the crude mixture 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 mixture was then stirred at room temperature for 2 hours. DMF was removed under vacuum and the crude residue was purified by column chromatography to provide 2-({[2,4-dichloro-1-(propan-2-yl)-1H-imidazol-5-yl]methyl}sulfanyl)-6-methylpyrimidin-4-ol (700 mg, 21% overall yield); 1H NMR (400 MHz, CD3OD): δ 1.59 (d, 6H), 2.24 (s, 3H), 4.56 (s, 2H), 4.59 (m, 1H), 6.03 (bs, 1H); M+333.

Workup

  1. customThe solvent was evaporated
  2. dissolutionthe crude mixture was dissolved in DMF (20 mL)
  3. stirringThe mixture was then stirred at room temperature for 2 hours
  4. customDMF was removed under vacuum
  5. customthe crude residue was purified by column chromatography

Sources & evidence

ORD record
ord-8c61e097696b4629aaa940e2dcce6a8c
Source dataset
uspto-grants-2016_04
Patent number
US09315521B2

Reaction notes

Loading…