Triethylamine → HCID 178429444, compound

HRID 630003Notes

Reaction equation

HRID 630003 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-40ceb29b09fe4f4f842b13954b0d77f0
Source dataset
uspto-grants-2016_04
Patent number
US09315521B2

Reaction notes

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