Triethylamine → HCID 178430797, compound

HRID 630261Notes

Reaction equation

HRID 630261 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-92cd2a470f314cbcb03af74f4afe0c25
Source dataset
uspto-grants-2016_04
Patent number
US09315521B2

Reaction notes

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