Potassium Carbonate → HCID 178436797, compound

HRID 577156Notes

Reaction equation

HRID 577156 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:22]([CH2:29][CH3:30])=[N:23][CH:24]=[CH:25][C:26]=1[CH2:27][CH3:28]>CN(C=O)C>[CH2:29]([C:22]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)=[C:26]([CH2:27][CH3:28])[CH:25]=[CH:24][N:23]=1)[CH3:30]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 595893693-(Bromomethyl)-2,4-diethylpyridineHCID 178516148HCID 178516148, compound

Product 1

HCID 178436797HCID 178436797, compoundYield 83.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

2-sulfanyl-6-(trifluoromethyl)pyrimidin-4-ol (592 mg, 3.0 mmol) was dissolved in anhydrous DMF (25 mL), and then potassium carbonate (1.25 g, 9.0 mmol) and 3-(bromomethyl)-2,4-diethylpyridine (3.6 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 3-12% DCM/MeOH to afford 2-{[(2,4-diethylpyridin-3-yl)methyl]sulfanyl}-6-(trifluoromethyl)pyrimidin-4-ol (860 mg, 69% yield for 2 steps); 1H NMR (400 MHz, DMSO-d6): δ 1.13-1.20 (m, 6H), 2.67 (q, J=7.5 Hz, 2H), 2.81 (q, J=7.5 Hz, 2H), 4.54 (s, 2H), 6.67 (s, 1H), 7.10 (d, J=5.1 Hz, 1H), 8.34 (d, J=5.1 Hz, 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 3-12% DCM/MeOH

Sources & evidence

ORD record
ord-29b7f05e6e1f44afa2053e8b2ff3727d
Source dataset
uspto-grants-2015_05
Patent number
US09040538B2

Reaction notes

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