2-Methoxyethylamine → 2-Chloro-N-(2-methoxyethyl)-6-((2,2,2-trifluoroethoxy)methyl)pyrimidin-4-amine

HRID 59093Notes

Reaction equation

HRID 59093 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][NH2:5].[Cl:6][C:7]1[N:12]=[C:11](Cl)[CH:10]=[C:9]([CH2:14][O:15][CH2:16][C:17]([F:20])([F:19])[F:18])[N:8]=1>CO.C(#N)C>[Cl:6][C:7]1[N:12]=[C:11]([NH:5][CH2:4][CH2:3][O:2][CH3:1])[CH:10]=[C:9]([CH2:14][O:15][CH2:16][C:17]([F:20])([F:18])[F:19])[N:8]=1

Participants

5

Reactant 2

HCID 80182-MethoxyethylamineHCID 1178209122,4-Dichloro-6-((2,2,2-trifluoroethoxy)methyl)pyrimidine

Product 1

HCID 1178213532-Chloro-N-(2-methoxyethyl)-6-((2,2,2-trifluoroethoxy)methyl)pyrimidin-4-amine

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6342AcetonitrileSolvent

Procedure

A solution of 2-methoxyethanamine (59 μl, 0.69 mmol) in MeOH (2 mL) was added dropwise to an ice-cold solution of 2,4-dichloro-6-((2,2,2-trifluoroethoxy)methyl)pyrimidine (66 mg, 0.25 mmol) in acetonitrile (2 mL). The reaction was stirred at rt over night. The reaction mixture was concentrated in vacuo and the crude was purified by preparative HPLC to give the title compound as a solid, 43 mg (57%).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customthe crude was purified by preparative HPLC

Sources & evidence

ORD record
ord-2beccdd62c29486694e76a38bb200270
Source dataset
uspto-grants-2016_09
Patent number
US09439904B2

Reaction notes

Loading…