Triethylamine → HCID 178516145, compound

HRID 577089Notes

Reaction equation

HRID 577089 reaction equation
Br[CH2:2][C:3]1[C:4]([Cl:10])=[N:5][CH:6]=[CH:7][C:8]=1[Cl:9].[SH:11][C:12]1[N:17]=[C:16]([OH:18])[CH:15]=[C:14]([C:19]([F:22])([F:21])[F:20])[N:13]=1.C(N(CC)CC)C>C(O)C>[Cl:10][C:4]1[C:3]([CH2:2][S:11][C:12]2[N:17]=[C:16]([OH:18])[CH:15]=[C:14]([C:19]([F:22])([F:20])[F:21])[N:13]=2)=[C:8]([Cl:9])[CH:7]=[CH:6][N:5]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 589517013-(Bromomethyl)-2,4-dichloropyridineHCID 178516148HCID 178516148, compound

Product 1

HCID 178516145HCID 178516145, compoundYield 22%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 3-(bromomethyl)-2,4-dichloropyridine (2.9 g, 12.3 mmol), 2-sulfanyl-6-(trifluoromethyl)pyrimidin-4-ol (1.2 g, 6.1 mmol), and triethylamine (1.3 mL, 9.3 mmol) in absolute ethanol (25 mL) was stirred at room temperature overnight. The mixture was evaporated to dryness. The residue was dissolved in EtOAc (80 mL). The solution was extracted with water (3×50 mL) and 1 N NaOH (1×50 mL). The organic layer was recovered, dried over MgSO4, filtered, evaporated, and dried in vacuo. The crude product was purified by flash chromatography (0-5% MeOH/DCM), affording the title compound (475 mg, 22% yield); 1H NMR (400 MHz, DMSO-d6): δ 4.75 (s, 2H), 6.72 (s, 1H), 7.69 (d, 1H, J=5.3 Hz), 8.36 (d, 1H, J=5.3 Hz); M+ 357.

Workup

  1. customThe mixture was evaporated to dryness
  2. dissolutionThe residue was dissolved in EtOAc (80 mL)
  3. extractionThe solution was extracted with water (3×50 mL) and 1 N NaOH (1×50 mL)
  4. customThe organic layer was recovered
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customevaporated
  8. customdried in vacuo
  9. customThe crude product was purified by flash chromatography (0-5% MeOH/DCM)

Sources & evidence

ORD record
ord-6ec295a479f049ca865a42dad51fc2ef
Source dataset
uspto-grants-2015_05
Patent number
US09040538B2

Reaction notes

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