2,4-Dichloro-1,3,5-triazine → HCID 22028111, compound

HRID 1815895Notes

Reaction equation

HRID 1815895 reaction equation
Cl[C:2]1[N:7]=[C:6]([Cl:8])[N:5]=[CH:4][N:3]=1.CCN(C(C)C)C(C)C.[NH2:18][C:19]1[CH:20]=[C:21]([O:27][CH3:28])[C:22]([O:25][CH3:26])=[CH:23][CH:24]=1>CN(C=O)C>[Cl:8][C:6]1[N:5]=[CH:4][N:3]=[C:2]([NH:18][C:19]2[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[C:21]([O:27][CH3:28])[CH:20]=2)[N:7]=1

Participants

5

Reactant 3

HCID 178102,4-Dichloro-1,3,5-triazineHCID 227703,4-DimethoxyanilineHCID 81531Diisopropylethylamine

Product 1

HCID 22028111HCID 22028111, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

2,4-Dichloro-1,3,5-triazine (12.6 g, 84 mmol) was dissolved into DMF (100 mL) under N2 and cooled to 0° C. DIEA (11.7 g, 90 mmol) was added, followed by 4-aminoveratrole (13.35 g, 87 mmol). The reaction solution was stirred with gradual warming to RT. The reaction was quenched after 3.5 h with water, which causes a gray precipitate to form. This precipitate was recovered by vacuum filtration, washed with cold water, dried under high vacuum, then eluted through a 28×4.5 cm column of silica gel (0.1% NH4OH(aq) buffered 1%, 2%, 3%, 4%, and 5% MeOH/CH2Cl2 step gradient) giving (4-chloro-[1,3,5]triazin-2-yl)-(3,4-dimethoxy-phenyl)-amine as an off white solid.

Workup

  1. temperaturewith gradual warming to RT
  2. customThe reaction was quenched after 3.5 h with water, which
  3. customto form
  4. filtrationThis precipitate was recovered by vacuum filtration
  5. washwashed with cold water
  6. customdried under high vacuum
  7. washeluted through a 28×4.5 cm column of silica gel (0.1% NH4OH(aq) buffered 1%, 2%, 3%, 4%, and 5% MeOH/CH2Cl2 step gradient)

Sources & evidence

ORD record
ord-f7c15ea2c0f44e80a7ebc3bcfcf7d5a4
Source dataset
uspto-grants-2005_04
Patent number
US06881737B2

Reaction notes

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