Triethylamine → HCID 178429450, compound

HRID 577239Notes

Reaction equation

HRID 577239 reaction equation
Br[CH2:2][C:3]1[C:8]([CH3:9])=[CH:7][N:6]=[CH:5][C:4]=1[CH3:10].[CH3:11][C:12]1[N:17]=[C:16]([SH:18])[N:15]=[C:14]([OH:19])[CH:13]=1.C(N(CC)CC)C>C(O)C>[CH3:10][C:4]1[CH:5]=[N:6][CH:7]=[C:8]([CH3:9])[C:3]=1[CH2:2][S:18][C:16]1[N:15]=[C:14]([OH:19])[CH:13]=[C:12]([CH3:11])[N:17]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 595894034-(Bromomethyl)-3,5-dimethylpyridineHCID 178429541HCID 178429541, compound

Product 1

HCID 178429450HCID 178429450, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a 0° C. mixture of 4-(bromomethyl)-3,5-dimethylpyridine (18.6 mmol) and 6-methyl-2-sulfanylpyrimidin-4-ol (1.7 g, 12 mmol) in absolute ethanol (170 mL) was added triethylamine (8 mL, 57.4 mmol). The mixture was stirred at room temperature overnight. The solid precipitate was removed by filtration. Diethyl ether (300 mL) was added to the filtrate. The precipitate was removed by filtration. The filtrate was recovered, evaporated, and co-evaporated with EtOAc (1×50 mL). The residue was treated with water (300 mL). The solid material was recovered by filtration, washed with water (4×30 mL), diethyl ether (3×30 mL) and hexanes (2×30 mL), and dried in vacuo, affording 2-{[(3,5-dimethylpyridin-4-yl)methyl]sulfanyl}-6-methylpyrimidin-4-ol (1.78 g, 57% yield). The product was used without further purification.

Workup

  1. customThe solid precipitate was removed by filtration
  2. additionDiethyl ether (300 mL) was added to the filtrate
  3. customThe precipitate was removed by filtration
  4. customThe filtrate was recovered
  5. customevaporated
  6. additionThe residue was treated with water (300 mL)
  7. filtrationThe solid material was recovered by filtration
  8. washwashed with water (4×30 mL), diethyl ether (3×30 mL) and hexanes (2×30 mL)
  9. customdried in vacuo

Sources & evidence

ORD record
ord-86394fe675dd40cd879a17f17dba6dda
Source dataset
uspto-grants-2015_05
Patent number
US09040538B2

Reaction notes

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