2,4-Dichloro-5-(trifluoromethyl)pyrimidine → HCID 86668788, compound

HRID 921278Notes

Reaction equation

HRID 921278 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([P:8](=[O:11])([CH3:10])[CH3:9])=[CH:4][CH:3]=1.Cl[C:13]1[N:18]=[C:17]([Cl:19])[C:16]([C:20]([F:23])([F:22])[F:21])=[CH:15][N:14]=1>CN(C)C(=O)C.C(N(C(C)C)CC)(C)C>[Cl:19][C:17]1[C:16]([C:20]([F:22])([F:21])[F:23])=[CH:15][N:14]=[C:13]([NH:1][C:2]2[CH:3]=[CH:4][C:5]([P:8]([CH3:9])([CH3:10])=[O:11])=[CH:6][CH:7]=2)[N:18]=1

Participants

5

Reactant 2

HCID 27827742,4-Dichloro-5-(trifluoromethyl)pyrimidineHCID 206345534-(Dimethylphosphoryl)aniline

Product 1

HCID 86668788HCID 86668788, compoundYield 494%

Reagents, catalysts & solvents 2

HCID 31374DimethylacetamideSolventHCID 81531DiisopropylethylamineSolvent

Procedure

A suspension of 4-amino-dimethylphenylphosphine oxide (3.7 g, 2.2 mmol) in 15 mL of N,N-Dimethylacetamide and 3.6 mL of Diisopropylethylamine, was allowed to stirred at room temperature for 15 minutes until a clear solution was obtained. 2,4-Dichloro-5-(trifluoromethyl)pyrimidine (5.7 g, 2.6 mmol) was added in four portions over 5 minutes. The reaction mixture was stirred at 60 degrees for 1 hour. The reaction mixture was cooled to room temperature and filtered to obtain a white solid. The white solid was washed with 50 mL of water three times and followed by 50 mL of Ethyl ether three times. The white solid was dried under vacuum to yield desired product (3.8 g, 49% yield). MS ES+: m/z=350.

Workup

  1. customwas obtained
  2. stirringThe reaction mixture was stirred at 60 degrees for 1 hour
  3. temperatureThe reaction mixture was cooled to room temperature
  4. filtrationfiltered
  5. customto obtain a white solid
  6. washThe white solid was washed with 50 mL of water three times
  7. customThe white solid was dried under vacuum

Sources & evidence

ORD record
ord-4f3e4992d0f244e89b1fc9ee984c8238
Source dataset
uspto-grants-2016_03
Patent number
US09273077B2

Reaction notes

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