Potassium Carbonate → HCID 178429504, compound

HRID 577133Notes

Reaction equation

HRID 577133 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+].Cl.Cl[CH2:18][C:19]1[N:23]([CH:24]2[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]2)[CH:22]=[N:21][CH:20]=1>CN(C=O)C>[CH:24]1([N:23]2[C:19]([CH2:18][S:8][C:6]3[N:5]=[C:4]([OH:9])[CH:3]=[C:2]([CH3:1])[N:7]=3)=[CH:20][N:21]=[CH:22]2)[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 53398878858220-96-9HCID 178429541HCID 178429541, compound

Product 1

HCID 178429504HCID 178429504, compoundYield 44%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

6-methyl-2-sulfanylpyrimidin-4-ol (1.1 g, 7.7 mmol) was dissolved in anhydrous DMF (40 mL), then potassium carbonate (3.19 g, 23.1 mmol) and 5-(chloromethyl)-1-cyclohexyl-1H-imidazole hydrochloride (8.5 mmol) in DMF (10 mL) were added. The mixture was stirred for 3.5 hours 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 12% DCM/MeOH to afford 2-{[(1-cyclohexyl-1H-imidazol-5-yl)methyl]sulfanyl)-6-methylpyrimidin-4-ol (770 mg, 44% yield); 1H NMR (500 MHz, DMSO-d6): δ 1.17-1.30 (m, 2H), 1.62-1.67 (m, 4H), 1.77-1.81 (m, 2H), 1.92-1.95 (m, 2H), 2.23 (s, 3H). 3.92-3.96 (m, 1H), 4.51 (s, 2H), 6.03 (s, 1H), 6.85 (s, 1H), 7.75 (s, 1H).

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 12% DCM/MeOH

Sources & evidence

ORD record
ord-0f75179aa02f43bfa2fb89f1ed191c84
Source dataset
uspto-grants-2015_05
Patent number
US09040538B2

Reaction notes

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