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

HRID 983423Notes

Reaction equation

HRID 983423 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) was 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) were added. The reaction mixture was kept at 0° C. for 15 to 30 min and at RT for 2 h. The reaction mixture was diluted with EtOAc and washed with brine. The organic layer was dried over Na2SO4, filtered, and evaporated in vacuo. The residue was added to CH2Cl2 and the resulting white precipitate was filtered and dried under reduced pressure to give (4-chloro-[1,3,5]triazin-2-yl)-(3,4,5-trimethoxy-phenyl)amine: MS m/z=279 [M−Cl+OH2]+. Calc'd for C12H13ClN4O3: 296.

Workup

  1. washwashed with brine
  2. dry with materialThe organic layer was dried over Na2SO4
  3. filtrationfiltered
  4. customevaporated in vacuo
  5. additionThe residue was added to CH2Cl2
  6. filtrationthe resulting white precipitate was filtered
  7. customdried under reduced pressure

Sources & evidence

ORD record
ord-997d739a799647c9899f558db2ab8997
Source dataset
uspto-grants-2005_03
Patent number
US06864255B2

Reaction notes

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