Potassium Carbonate → HCID 178429508, compound

HRID 577045Notes

Reaction equation

HRID 577045 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])[CH:21]=[N:20][CH:19]=1>CN(C=O)C>[CH3:1][C:2]1[N:7]=[C:6]([S:8][CH2:17][C:18]2[N:22]([CH3:23])[CH:21]=[N:20][CH:19]=2)[N:5]=[C:4]([OH:9])[CH:3]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 534271275-(Bromomethyl)-1-methyl-1H-imidazoleHCID 178429541HCID 178429541, compound

Product 1

HCID 178429508HCID 178429508, compoundYield 42.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

6-methyl-2-sulfanylpyrimidin-4-ol (846 mg, 5.9 mmol) was dissolved in anhydrous DMF (40 mL), then potassium carbonate (2.46 g, 17.8 mmol) and 5-(bromomethyl)-1-methyl-1H-imidazole (1.56 g, 8.9 mmol) were added. The mixture was stirred for 4 hours at room temperature. The solid was removed by filtration, washed with methanol, and the filtrate was evaporated. The residue was dissolved in DCM/MeOH and purified on silica gel using 10% DCM in MeOH to afford 6-methyl-2-{[(1-methyl-1H-imidazol-5-yl)methyl]sulfanyl}pyrimidin-4-ol (589 mg, 42% yield for 2 steps); 1H NMR (400 MHz, DMSO-d6): δ 2.22 (s, 3H), 3.61 (s, 3H), 4.44 (s, 2H), 6.02 (s, 1H), 6.88 (s, 1H), 7.56 (s, 1H); LRMS (ES+) m/z 237 (100%, 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 10% DCM in MeOH

Sources & evidence

ORD record
ord-3c51aad0349e4e6dab025cc314f8dfd7
Source dataset
uspto-grants-2015_05
Patent number
US09040538B2

Reaction notes

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