Triethylamine → HCID 178462820, compound

HRID 630077Notes

Reaction equation

HRID 630077 reaction equation
[CH2:1]([N:3]1[C:7]([CH2:8]O)=[CH:6][N:5]=[CH:4]1)[CH3:2].BrP(Br)Br.[CH3:14][C:15]1[N:20]=[C:19]([SH:21])[N:18]=[C:17]([OH:22])[CH:16]=1.C(N(CC)CC)C>ClCCl>[CH2:1]([N:3]1[C:7]([CH2:8][S:21][C:19]2[N:18]=[C:17]([OH:22])[CH:16]=[C:15]([CH3:14])[N:20]=2)=[CH:6][N:5]=[CH:4]1)[CH3:2]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 24614Phosphorus tribromideHCID 22988641(1-Ethyl-1H-imidazol-5-yl)methanolHCID 178429541HCID 178429541, compound

Product 1

HCID 178462820HCID 178462820, compoundYield 12%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (1-ethyl-1H-imidazol-5-yl)methanol (631 mg, 5.0 mmol) in dichloromethane (20 mL) was added dropwise tribromophosphane (0.94 mL, 10.0 mmol). The resulting mixture was stirred at room temperature for 6 hours. After evaporation, the crude 5-(bromomethyl)-1-ethyl-1H-imidazole was dissolved in cold ethanol (30 mL), and 6-methyl-2-sulfanylpyrimidin-4-ol (700 mg, 5 mmol) and triethylamine (2.8 mL, 20 mmol) were added. After 2 hours, the solvent was evaporated, and the residue was purified by chromatography (4% methanol in dichloromethane) to provide a white solid (150 mg, 12% yield); 1H NMR (400 MHz, DMSO-d6): δ 1.33 (t, 3H), 2.22 (s, 3H), 4.02 (q, 2H), 4.46 (s, 2H), 6.03 (br, 1H), 6.88 (s, 1H), 7.64 (s, 1H); M+251.

Workup

  1. customAfter evaporation
  2. dissolutionthe crude 5-(bromomethyl)-1-ethyl-1H-imidazole was dissolved in cold ethanol (30 mL)
  3. waitAfter 2 hours
  4. customthe solvent was evaporated
  5. customthe residue was purified by chromatography (4% methanol in dichloromethane)

Sources & evidence

ORD record
ord-15b6ff6876a64c9884daabb2fccb2770
Source dataset
uspto-grants-2016_04
Patent number
US09315521B2

Reaction notes

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