Triethylamine → 6-methyl-2-(pyridin-3-ylmethylsulfanyl)-1H-pyrimidin-4-one

HRID 576920Notes

Reaction equation

HRID 576920 reaction equation
[Br-].Br[CH2:3][C:4]1[CH:5]=[NH+:6][CH:7]=[CH:8][CH:9]=1.[CH3:10][C:11]1[N:16]=[C:15]([SH:17])[N:14]=[C:13]([OH:18])[CH:12]=1.C(N(CC)CC)C>C(O)C>[CH3:10][C:11]1[N:16]=[C:15]([S:17][CH2:3][C:4]2[CH:5]=[N:6][CH:7]=[CH:8][CH:9]=2)[N:14]=[C:13]([OH:18])[CH:12]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 687735083-Bromomethylpyridinium bromideHCID 178429541HCID 178429541, compound

Product 1

HCID 1784294466-methyl-2-(pyridin-3-ylmethylsulfanyl)-1H-pyrimidin-4-oneYield 39%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture 3-(bromomethyl)pyridin-1-ium bromide (550 mg, 2.5 mmol), 6-methyl-2-sulfanylpyrimidin-4-ol (285 mg, 2.0 mmol), and triethylamine (1.1 mL, 8.0 mmol) in absolute ethanol (10 mL) was stirred at room temperature overnight. The solid residue was removed by filtration. The filtrate was recovered and evaporated under reduced pressure. The solid product was suspended in acetone (50 mL). The solid material was removed by filtration. The filtrate was recovered and evaporated to dryness. The residue was suspended in water (50 mL). The product was recovered by filtration, washed with diethyl ether (2×20 mL), and dried in vacuo, affording 6-methyl-2-[(pyridin-3-ylmethyl)sulfanyl]pyrimidin-4-ol (181 mg, 39% yield); 1H NMR (400 MHz, DMSO-d6): δ 2.19 (s, 3H), 4.36 (s, 2H), 6.00 (s (br), 1H), 7.32 (td, 1H, J=0.8 Hz, 7.8 Hz), 7.82 (dd, 1H, J=0.8 Hz, 7.8 Hz), 8.42 (dd, 1H, J=0.8 Hz, 4.7 Hz), 8.61 (d, 1H, J=1.8 Hz); M+ 234; HPLC purity: 98.1%.

Workup

  1. customThe solid residue was removed by filtration
  2. customThe filtrate was recovered
  3. customevaporated under reduced pressure
  4. customThe solid material was removed by filtration
  5. customThe filtrate was recovered
  6. customevaporated to dryness
  7. filtrationThe product was recovered by filtration
  8. washwashed with diethyl ether (2×20 mL)
  9. customdried in vacuo

Sources & evidence

ORD record
ord-71d8261aed8645978cf67f9aee5fe662
Source dataset
uspto-grants-2015_05
Patent number
US09040538B2

Reaction notes

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