Triethylamine → HCID 178429444, compound

HRID 576962Notes

Reaction equation

HRID 576962 reaction equation
Br[CH2:2][C:3]1[C:4]([Cl:9])=[N:5][CH:6]=[CH:7][CH:8]=1.[CH3:10][C:11]1[N:16]=[C:15]([SH:17])[N:14]=[C:13]([OH:18])[CH:12]=1.C(N(CC)CC)C>C(O)C>[ClH:9].[Cl:9][C:4]1[C:3]([CH2:2][S:17][C:15]2[N:14]=[C:13]([OH:18])[CH:12]=[C:11]([CH3:10])[N:16]=2)=[CH:8][CH:7]=[CH:6][N:5]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 189310283-(Bromomethyl)-2-chloropyridineHCID 178429541HCID 178429541, compound

Product 1

HCID 178429444HCID 178429444, compoundYield 54.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 3-(bromomethyl)-2-chloropyridine (1.0 g, 4.8 mmol), 6-methyl-2-sulfanylpyrimidin-4-ol (570 mg, 4.0 mmol), and triethylamine (1.4 mL, 10.0 mmol) in absolute ethanol (20 mL) was stirred at room temperature overnight. The product was recovered by filtration, washed with EtOH (15 mL), diethyl ether (3×15 mL), water (3×30 mL), and hexanes (3×15 mL). The solid material was dried in vacuo, affording the 2-{[(2-chloropyridin-3-yl)methyl]sulfanyl}-6-methylpyrimidin-4-ol (400 mg, 31% yield). The product was used without further purification.

Workup

  1. filtrationThe product was recovered by filtration
  2. washwashed with EtOH (15 mL), diethyl ether (3×15 mL), water (3×30 mL), and hexanes (3×15 mL)
  3. customThe solid material was dried in vacuo

Sources & evidence

ORD record
ord-76a04cb448c6470f9b96e0cfbc4c81dd
Source dataset
uspto-grants-2015_05
Patent number
US09040538B2

Reaction notes

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