Potassium Carbonate → HCID 178437119, compound

HRID 630224Notes

Reaction equation

HRID 630224 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:23]=[CH:22][N:21]=[CH:20][C:19]=1[CH2:24][CH3:25]>CN(C=O)C>[CH2:24]([C:19]1[CH:20]=[N:21][CH:22]=[CH:23][C:18]=1[CH2:17][S:8][C:6]1[N:5]=[C:4]([OH:9])[CH:3]=[C:2]([CH3:1])[N:7]=1)[CH3:25]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 595893414-(Bromomethyl)-3-ethylpyridineHCID 178429541HCID 178429541, compound

Product 1

HCID 178437119HCID 178437119, compoundYield 7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

6-methyl-2-sulfanylpyrimidin-4-ol (686 mg, 4.8 mmol) was dissolved in anhydrous DMF (30 mL), and then potassium carbonate (2.0 g, 14.5 mmol) and 4-(bromomethyl)-3-ethylpyridine (5.8 mmol) in DMF (10 mL) were added. The mixture was stirred for 2.5 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 3-12% DCM/MeOH to afford 2-{[(3-ethylpyridin-4-yl)methyl]sulfanyl)-6-methylpyrimidin-4-ol (88 mg, 6% yield for 3 steps).

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-8990f739d324448083c626366d51bf3f
Source dataset
uspto-grants-2016_04
Patent number
US09315521B2

Reaction notes

Loading…