2,4-Dichloro-1,3,5-triazine → HCID 22028121, compound

HRID 1815893Notes

Reaction equation

HRID 1815893 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.[CH3:18][O:19][C:20]1[CH:21]=[C:22]([CH:24]=[C:25]([O:29][CH3:30])[C:26]=1[O:27][CH3:28])[NH2:23]>CN(C=O)C.CCOC(C)=O>[Cl:8][C:6]1[N:5]=[CH:4][N:3]=[C:2]([NH:23][C:22]2[CH:24]=[C:25]([O:29][CH3:30])[C:26]([O:27][CH3:28])=[C:20]([O:19][CH3:18])[CH:21]=2)[N:7]=1

Participants

6

Reactant 3

HCID 178102,4-Dichloro-1,3,5-triazineHCID 322853,4,5-TrimethoxyanilineHCID 81531Diisopropylethylamine

Product 1

HCID 22028121HCID 22028121, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

2,4-Dichloro-1,3,5-triazine (1.054 g, 7.028 mmol) is dissolved in DMF (5 ml) and cooled to 0° C. To this solution, DIEA (1.225 ml, 7.028 mmol) and 3,4,5-trimethoxyaniline (1.185 g, 6.47 mmol) are added. The reaction mixture is kept at 0° C. for 15 to 30 min and at RT for about 2 h. The reaction mixture is diluted with EtOAc and washed with brine. The organic layer is dried over Na2SO41 filtered, and evaporated in vacuo. The residue is added to CH2Cl2 and the resulting white precipitate is filtered and dried under reduced pressure to give (4-chloro-[1,3,5]triazin-2-yl)-(3,4,5-trimethoxy-phenyl)amine.

Workup

  1. washwashed with brine
  2. customThe organic layer is dried over Na2SO41
  3. filtrationfiltered
  4. customevaporated in vacuo
  5. additionThe residue is added to CH2Cl2
  6. filtrationthe resulting white precipitate is filtered
  7. customdried under reduced pressure

Sources & evidence

ORD record
ord-199a9134934b46419a0a0ae1346cef67
Source dataset
uspto-grants-2005_04
Patent number
US06881737B2

Reaction notes

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