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

HRID 1471996Notes

Reaction equation

HRID 1471996 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-148fe0917bc849e0ba6a74dd04d62fce
Source dataset
uspto-grants-2015_04
Patent number
US09012462B2

Reaction notes

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