Potassium Carbonate → HCID 178429500, compound

HRID 630099Notes

Reaction equation

HRID 630099 reaction equation
[CH3:1][C:2]1[N:7]=[C:6]([SH:8])[N:5]=[C:4]([OH:9])[CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:17][C:18]1[N:22]([CH3:23])[C:21]([CH3:24])=[N:20][CH:19]=1>CN(C=O)C>[CH3:23][N:22]1[C:18]([CH2:17][S:8][C:6]2[N:5]=[C:4]([OH:9])[CH:3]=[C:2]([CH3:1])[N:7]=2)=[CH:19][N:20]=[C:21]1[CH3:24]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 59589490HCID 59589490, compoundHCID 178429541HCID 178429541, compound

Product 1

HCID 178429500HCID 178429500, compoundYield 21%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

6-methyl-2-sulfanylpyrimidin-4-ol (764 mg, 5.4 mmol) was dissolved in anhydrous DMF (30 mL), then potassium carbonate (2.23 g, 16.1 mmol) and 5-(bromomethyl)-1,2-dimethyl-1H-imidazole (1.52 g, 8.1 mmol) were added. The mixture was stirred overnight at room temperature. The solid was removed by filtration and washed with methanol, and the filtrate was evaporated. The residue was dissolved in DCM/MeOH and purified on silica gel using 20% DCM in MeOH to afford 2-{[(1,2-dimethyl-1H-imidazol-5-yl)methyl]sulfanyl}-6-methylpyrimidin-4-ol (279 mg, 21% yield for 3 steps); 1H NMR (400 MHz, DMSO-d6): δ 2.20 (s, 3H), 2.24 (s, 3H), 3.46 (s, 3H), 4.40 (s, 2H), 5.99 (s, 1H), 6.72 (s, 1H); LRMS (ES+) m/z 251 (50%, M+1).

Workup

  1. customThe solid was removed by filtration
  2. washwashed with methanol
  3. customthe filtrate was evaporated
  4. dissolutionThe residue was dissolved in DCM/MeOH
  5. custompurified on silica gel using 20% DCM in MeOH

Sources & evidence

ORD record
ord-34b4449922204cebb8cfcbb393f54758
Source dataset
uspto-grants-2016_04
Patent number
US09315521B2

Reaction notes

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