Triethylamine → HCID 59589309, compound

HRID 630210Notes

Reaction equation

HRID 630210 reaction equation
Br.Br[CH2:3][C:4]1[C:9]([Cl:10])=[CH:8][N:7]=[CH:6][C:5]=1[Cl:11].Cl.[CH3:13][C:14]1[CH:19]=[CH:18][N:17]=[C:16]([SH:20])[N:15]=1.C(N(CC)CC)C>CCO>[Cl:11][C:5]1[CH:6]=[N:7][CH:8]=[C:9]([Cl:10])[C:4]=1[CH2:3][S:20][C:16]1[N:15]=[C:14]([CH3:13])[CH:19]=[CH:18][N:17]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 668153104-(Bromomethyl)-3,5-dichloropyridine hydrobromideHCID 1784286872-Mercapto-4-methylpyrimidine hydrochloride

Product 1

HCID 59589309HCID 59589309, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 4-(bromomethyl)-3,5-dichloropyridine hydrobromide (1.3 g, 5.0 mmol), 4-methylpyrimidine-2-thiol hydrochloride (543 mg, 3.3 mmol), and triethylamine (1.8 mL, 12.9 mmol) in absolute EtOH (35 mL) was stirred at room temperature overnight. The mixture was evaporated, co-evaporated with EtOAc (10 mL), and dried in vacuo. The solid residue was treated with water (75 mL). The mixture was extracted with 50% ethyl acetate/Et2O (75 mL). The organic extract was extracted with brine (2×75 mL), dried over MgSO4, filtered, evaporated, and dried in vacuo. The crude product was purified by flash chromatography (0-4% MeOH/CH2Cl2), affording the title compound (800 mg, 85% yield); 1H NMR (400 MHz, DMSO-d6): δ 2.45 (s, 3H), 4.70 (s, 2H), 7.17 (d, 1H, J=5.1 Hz), 8.54 (d, 1H, J=5.1 Hz), 8.67 (s, 2H); M+287.

Workup

  1. customThe mixture was evaporated
  2. customdried in vacuo
  3. additionThe solid residue was treated with water (75 mL)
  4. extractionThe mixture was extracted with 50% ethyl acetate/Et2O (75 mL)
  5. extractionThe organic extract
  6. extractionwas extracted with brine (2×75 mL)
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. customevaporated
  10. customdried in vacuo
  11. customThe crude product was purified by flash chromatography (0-4% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-bba0efb28cc74ea1ba12ece69a853a75
Source dataset
uspto-grants-2016_04
Patent number
US09315521B2

Reaction notes

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