2,4-Dichloro-5-(trifluoromethyl)pyrimidine → 4-Chloro-2-[6-(dimethylphosphoryl)-2-methoxypyridin-3-yl]-5-(trifluoromethyl)pyrimidine

HRID 921332Notes

Reaction equation

HRID 921332 reaction equation
[CH3:1][P:2]([C:5]1[N:10]=[C:9]([O:11][CH3:12])[C:8](N)=[CH:7][CH:6]=1)([CH3:4])=[O:3].Cl[C:15]1[N:20]=[C:19]([Cl:21])[C:18]([C:22]([F:25])([F:24])[F:23])=[CH:17][N:16]=1>CN(C)C(=O)C.C(N(C(C)C)CC)(C)C>[Cl:21][C:19]1[C:18]([C:22]([F:24])([F:23])[F:25])=[CH:17][N:16]=[C:15]([C:8]2[C:9]([O:11][CH3:12])=[N:10][C:5]([P:2]([CH3:4])([CH3:1])=[O:3])=[CH:6][CH:7]=2)[N:20]=1

Participants

5

Reactant 2

HCID 27827742,4-Dichloro-5-(trifluoromethyl)pyrimidineHCID 67052694(5-Amino-6-methoxypyridin-2-yl)dimethylphosphine oxide

Product 1

HCID 866687954-Chloro-2-[6-(dimethylphosphoryl)-2-methoxypyridin-3-yl]-5-(trifluoromethyl)pyrimidine

Reagents, catalysts & solvents 2

HCID 31374DimethylacetamideSolventHCID 81531DiisopropylethylamineSolvent

Procedure

A suspension of 6-(dimethylphosphoryl)-2-methoxypyridin-3-ylamine (prepared in Example 32: 2.2 mmol) in 15 mL of N,N-Dimethylacetamide and 3.6 mL of Diisopropylethylamine, is allowed to stirred at room temperature for 15 minutes until a clear solution is obtained. 2,4-Dichloro-5-(trifluoromethyl)pyrimidine (5.7 g, 2.6 mmol) is added in four portions over 5 minutes. The reaction mixture is stirred at 60 degrees for 1 hour. The reaction mixture is cooled to room temperature and filtered to obtain a white solid. The white solid is washed with 50 mL of water three times and followed by 50 mL of Ethyl ether three times. The white solid is dried under vacuum to yield 4-chloro-2-[6-(dimethylphosphoryl)-2-methoxypyridin-3-yl]-5-(trifluoromethyl)pyrimidine.

Workup

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

Sources & evidence

ORD record
ord-bc6b99bb8e854e40a277921279b91a86
Source dataset
uspto-grants-2016_03
Patent number
US09273077B2

Reaction notes

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