Triethylamine → 6-methyl-2-(pyridin-4-ylmethylsulfanyl)-1H-pyrimidin-4-one

HRID 629975Notes

Reaction equation

HRID 629975 reaction equation
[CH3:1][C:2]1[N:7]=[C:6]([SH:8])[N:5]=[C:4]([OH:9])[CH:3]=1.C(N(CC)CC)C.[Br-].Br[CH2:19][C:20]1[CH:25]=[CH:24][NH+:23]=[CH:22][CH:21]=1>C(O)C.O>[CH3:1][C:2]1[N:7]=[C:6]([S:8][CH2:19][C:20]2[CH:25]=[CH:24][N:23]=[CH:22][CH:21]=2)[N:5]=[C:4]([OH:9])[CH:3]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 57969416CID 57969416HCID 178429541HCID 178429541, compound

Product 1

HCID 1784294706-methyl-2-(pyridin-4-ylmethylsulfanyl)-1H-pyrimidin-4-oneYield 26.1%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

6-methyl-2-sulfanylpyrimidin-4-ol (300 mg, 2.1 mmol) was dissolved in absolute ethanol (10 mL), then triethylamine (650 μL, 4.6 mmol) and 4-(bromomethyl)pyridin-1-ium bromide (587 mg, 2.3 mmol) were added. The mixture was stirred overnight at room temperature, and the solvent was evaporated. The residue was dissolved in DCM and purified on silica gel using 10% DCM/MeOH to afford, after washing with water, 6-methyl-2-[(pyridin-4-ylmethyl)sulfanyl]pyrimidin-4-ol as white solid (128 mg, 26% yield); 1H NMR (400 MHz, MeOd4): δ 2.24 (s, 3H), 4.47 (s, 2H), 6.00 (s, 1H), 7.52 (dd, J=4.5 Hz, J=1.6 Hz, 2H), 8.45 (dd, J=4.5 Hz, J=1.6 Hz, 2H).

Workup

  1. customthe solvent was evaporated
  2. dissolutionThe residue was dissolved in DCM
  3. custompurified on silica gel using 10% DCM/MeOH
  4. customto afford

Sources & evidence

ORD record
ord-b5f3cc2721ec4b4a9ab60e29bcb700ed
Source dataset
uspto-grants-2016_04
Patent number
US09315521B2

Reaction notes

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