Potassium Carbonate → HCID 178480367, compound

HRID 577143Notes

Reaction equation

HRID 577143 reaction equation
[SH:1][C:2]1[N:7]=[C:6]([OH:8])[CH:5]=[C:4]([C:9]([F:12])([F:11])[F:10])[N:3]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:20][C:21]1[C:25]([Cl:26])=[CH:24][N:23]([CH3:27])[N:22]=1>CN(C=O)C>[Cl:26][C:25]1[C:21]([CH2:20][S:1][C:2]2[N:7]=[C:6]([OH:8])[CH:5]=[C:4]([C:9]([F:12])([F:10])[F:11])[N:3]=2)=[N:22][N:23]([CH3:27])[CH:24]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 595893993-(bromomethyl)-4-chloro-1-methyl-1H-pyrazoleHCID 178516148HCID 178516148, compound

Product 1

HCID 178480367HCID 178480367, compoundYield 11.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-sulfanyl-6-(trifluoromethyl)pyrimidin-4-ol (721 mg, 3.7 mmol) was dissolved in anhydrous DMF (20 mL), and then potassium carbonate (1.53 g, 11.0 mmol) and 3-(bromomethyl)-4-chloro-1-methyl-1H-pyrazole (4.7 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 4-10% DCM/MeOH to afford 2-{[(4-chloro-1-methyl-1H-pyrazol-3-yl)methyl]sulfanyl}-6-(trifluoromethyl)pyrimidin-4-ol (135 mg, 11% yield for 2 steps); 1H NMR (400 MHz, DMSO-d6): δ 3.78 (s, 3H), 4.39 (s, 2H), 6.66 (s, 1H), 7.93 (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 4-10% DCM/MeOH

Sources & evidence

ORD record
ord-c7dcb82e7eca485b80322bbdd61b3365
Source dataset
uspto-grants-2015_05
Patent number
US09040538B2

Reaction notes

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