Water → (6-Chloro-2-methylsulfanyl-pyrimidin-4-yl)-[2-(2,4-dichloro-phenyl)-ethyl]-amine

HRID 2110768Notes

Reaction equation

HRID 2110768 reaction equation
Cl[C:2]1[CH:7]=[C:6]([Cl:8])[N:5]=[C:4]([S:9][CH3:10])[N:3]=1.[Cl:11][C:12]1[CH:17]=[C:16]([Cl:18])[CH:15]=[CH:14][C:13]=1[CH2:19][CH2:20][NH2:21].C(=O)(O)[O-].[Na+].O>CCO>[Cl:8][C:6]1[N:5]=[C:4]([S:9][CH3:10])[N:3]=[C:2]([NH:21][CH2:20][CH2:19][C:13]2[CH:14]=[CH:15][C:16]([Cl:18])=[CH:17][C:12]=2[Cl:11])[CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 805314,6-Dichloro-2-(methylthio)pyrimidineHCID 1429382,4-DichlorophenethylamineHCID 516892Sodium Bicarbonate

Product 1

HCID 80545555(6-Chloro-2-methylsulfanyl-pyrimidin-4-yl)-[2-(2,4-dichloro-phenyl)-ethyl]-amineYield 72.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
85 °C

Procedure

A mixture of 4,6-dichloro-2-methylsulfanyl-pyrimidine (2.66 g, 13.6 mmol), 2-(2,4-dichloro-phenyl)-ethylamine (2.26 mL, 15 mmol) and sodium bicarbonate (2.29 g, 27.2 mmol) in EtOH (35 mL) is heated to 85° C. for 1 hour and poured into water (100 mL). The solid precipitate is collected by filtration and dissolved in hot EtOH (75 mL). After cooling overnight the crystals that formed are collected by filtration and dried to afford (6-chloro-2-methylsulfanyl-pyrimidin-4-yl)-[2-(2,4-dichloro-phenyl)-ethyl]-amine (3.43 g, 72%) as a solid.

Workup

  1. filtrationThe solid precipitate is collected by filtration
  2. dissolutiondissolved in hot EtOH (75 mL)
  3. temperatureAfter cooling overnight the crystals
  4. customthat formed
  5. filtrationare collected by filtration
  6. customdried

Sources & evidence

ORD record
ord-4914d54d312b4051b04ad0068588709d
Source dataset
uspto-grants-2009_04
Patent number
US07517889B2

Reaction notes

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