Homoveratrylamine → (6-Chloro-2-methylsulfanyl-pyrimidin-4-yl)-[2-(3,4-dimethoxy-phenyl)-ethyl]-amine

HRID 2110646Notes

Reaction equation

HRID 2110646 reaction equation
Cl[C:2]1[CH:7]=[C:6]([Cl:8])[N:5]=[C:4]([S:9][CH3:10])[N:3]=1.[CH3:11][O:12][C:13]1[CH:14]=[C:15]([CH2:21][CH2:22][NH2:23])[CH:16]=[CH:17][C:18]=1[O:19][CH3:20].C(=O)(O)[O-].[Na+]>CCO.O>[Cl:8][C:6]1[N:5]=[C:4]([S:9][CH3:10])[N:3]=[C:2]([NH:23][CH2:22][CH2:21][C:15]2[CH:16]=[CH:17][C:18]([O:19][CH3:20])=[C:13]([O:12][CH3:11])[CH:14]=2)[CH:7]=1

Participants

6

Reactant 3

HCID 8421Homoveratrylamine2×HCID 805314,6-Dichloro-2-(methylthio)pyrimidine2×HCID 516892Sodium Bicarbonate

Product 1

HCID 57636020(6-Chloro-2-methylsulfanyl-pyrimidin-4-yl)-[2-(3,4-dimethoxy-phenyl)-ethyl]-amineYield 103.9%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
85 °C

Procedure

A mixture of 4,6-dichloro-2-methylsulfanyl-pyrimidine [1 g, 5.1 mmol, Intermediate (29)], 3,4-dimethoxy-phenylethylamine [0.98 g, 5.4 mmol, Intermediate (30)], and sodium bicarbonate (0.86 g, 10 mmol) in EtOH (5 mL) is heated to reflux. After stirring at 85° C. for 4 hours the mixture is diluted with water and filtered. The solid is washed with water, and dried to afford (6-chloro-2-methylsulfanyl-pyrimidin-4-yl)-[2-(3,4-dimethoxy-phenyl)-ethyl]-amine [1.8 g, Intermediate (31)]. LCMS: RT=3.25 minutes, MS: 340 (M+H).

Workup

  1. temperatureis heated to reflux
  2. filtrationfiltered
  3. washThe solid is washed with water
  4. customdried

Sources & evidence

ORD record
ord-09df0b79927f4191a9e2cc59299a62b0
Source dataset
uspto-grants-2009_04
Patent number
US07517889B2

Reaction notes

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