Potassium Carbonate → HCID 178429493, compound

HRID 630206Notes

Reaction equation

HRID 630206 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[CH:19]=[N:20][CH:21]=[CH:22][C:23]=1[C:24]([F:27])([F:26])[F:25]>CN(C=O)C>[CH3:1][C:2]1[N:7]=[C:6]([S:8][CH2:17][C:18]2[CH:19]=[N:20][CH:21]=[CH:22][C:23]=2[C:24]([F:27])([F:25])[F:26])[N:5]=[C:4]([OH:9])[CH:3]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 178629043-(Bromomethyl)-4-(trifluoromethyl)pyridineHCID 178429541HCID 178429541, compound

Product 1

HCID 178429493HCID 178429493, compoundYield 27.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

6-methyl-2-sulfanylpyrimidin-4-ol (604 mg, 4.2 mmol) was dissolved in anhydrous DMF (30 mL), and then potassium carbonate (1.76 g, 12.8 mmol) and 3-(bromomethyl)-4-(trifluoromethyl)pyridine (5.5 mmol) in DMF (10 mL) 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 12% DCM/MeOH to afford 6-methyl-2-({[4-(trifluoromethyl)pyridin-3-yl]methyl}sulfanyl)pyrimidin-4-ol (349 mg, 21% yield for 2 steps); 1H NMR (400 MHz, DMSO-d6): δ 2.22 (s, 3H), 4.59 (s, 2H), 6.07 (bs, 1H), 7.75 (d, J=5.3 Hz, 1H), 8.76 (d, J=5.1 Hz, 1H), 9.02 (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-cd5bcf4040244bfdbb47578ebb1eeb00
Source dataset
uspto-grants-2016_04
Patent number
US09315521B2

Reaction notes

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