Triethylamine → HCID 178430797, compound

HRID 577219Notes

Reaction equation

HRID 577219 reaction equation
Br[CH2:2][C:3]1[C:8]([Cl:9])=[CH:7][N:6]=[CH:5][C:4]=1[Cl:10].[CH3:11][C:12]1[C:13]([OH:19])=[N:14][C:15]([SH:18])=[N:16][CH:17]=1.C(N(CC)CC)C>C(O)C>[Cl:10][C:4]1[CH:5]=[N:6][CH:7]=[C:8]([Cl:9])[C:3]=1[CH2:2][S:18][C:15]1[N:14]=[C:13]([OH:19])[C:12]([CH3:11])=[CH:17][N:16]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 222277664-(Bromomethyl)-3,5-dichloropyridineHCID 178430804HCID 178430804, compound

Product 1

HCID 178430797HCID 178430797, compoundYield 100.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a mixture of 4-(bromomethyl)-3,5-dichloropyridine (1.0 g, 4.15 mmol) and 5-methyl-2-sulfanylpyrimidin-4-ol (0.38 g, 2.69 mmol) in anhydrous ethanol (25 mL) at 0° C. was added triethylamine (1.67 g, 16.6 mmol). The reaction mixture was stirred at room temperature overnight. The solvent was evaporated, water was added, and the mixture was sonicated and then filtered. The solid was washed with water and hexane to provide 2-{[(3,5-dichloropyridin-4-yl)methyl]sulfanyl}-5-methylpyrimidin-4-ol (0.817 g, 65% yield); 1H NMR (400 MHz, DMSO-d6): δ 1.90 (s, 3H), 4.66 (s, 2H), 7.99 (s 1H), 8.66 (s, 2H); M+ 302.5.

Workup

  1. customThe solvent was evaporated
  2. additionwater was added
  3. customthe mixture was sonicated
  4. filtrationfiltered
  5. washThe solid was washed with water and hexane

Sources & evidence

ORD record
ord-d39317d828014e3b9dac42cbd39f0472
Source dataset
uspto-grants-2015_05
Patent number
US09040538B2

Reaction notes

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