Triethylamine → HCID 178429430, compound

HRID 577001Notes

Reaction equation

HRID 577001 reaction equation
Br[CH2:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[N:9]=[CH:8][CH:7]=[N:6]2.[CH3:13][C:14]1[N:19]=[C:18]([SH:20])[N:17]=[C:16]([OH:21])[CH:15]=1.C(N(CC)CC)C>C(O)C>[CH3:13][C:14]1[N:19]=[C:18]([S:20][CH2:2][C:3]2[CH:4]=[C:5]3[C:10](=[CH:11][CH:12]=2)[N:9]=[CH:8][CH:7]=[N:6]3)[N:17]=[C:16]([OH:21])[CH:15]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 102145106-(Bromomethyl)quinoxalineHCID 178429541HCID 178429541, compound

Product 1

HCID 178429430HCID 178429430, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 6-(bromomethyl)quinoxaline (900 mg, 4.0 mmol), 6-methyl-2-sulfanylpyrimidin-4-ol (440 mg, 3.1 mmol), and triethylamine (1.1 mL, 7.8 mmol) in absolute ethanol (20 mL) was stirred at room temperature overnight. The reaction mixture was evaporated and then co-evaporated with EtOAc. The solid residue was treated with water (100 mL). The solid product was recovered by filtration, washed with water (2×20 mL), diethyl ether (3×20 mL), and hexanes (3×20 mL), and then dried in vacuo, affording 6-methyl-2-[(quinoxalin-6-ylmethyl)sulfanyl]pyrimidin-4-ol (658 mg, 75% yield). The product was used without further purification.

Workup

  1. customThe reaction mixture was evaporated
  2. additionThe solid residue was treated with water (100 mL)
  3. filtrationThe solid product was recovered by filtration
  4. washwashed with water (2×20 mL), diethyl ether (3×20 mL), and hexanes (3×20 mL)
  5. customdried in vacuo

Sources & evidence

ORD record
ord-3971683e568649aeb2c7cbf0914ea628
Source dataset
uspto-grants-2015_05
Patent number
US09040538B2

Reaction notes

Loading…