Diethyl chlorophosphate → 4-[3-chloro-5-(trifluoromethyl)phenyl]-N-diethoxyphosphoryl-2-pyrimidin-2-yl-5-(trifluoromethyl)pyrazol-3-amine

HRID 705711Notes

Reaction equation

HRID 705711 reaction equation
[Cl:1][C:2]1[C:7]2OCO[C:6]=2[CH:5]=[C:4]([C:11]2[C:15]([C:16]([F:19])([F:18])[F:17])=[N:14][N:13]([C:20]3[N:25]=[CH:24][CH:23]=[CH:22][N:21]=3)[C:12]=2[NH2:26])[CH:3]=1.[H-].[Na+].[P:29](Cl)([O:34][CH2:35][CH3:36])([O:31][CH2:32][CH3:33])=[O:30]>O1CCCC1.O>[Cl:1][C:2]1[CH:3]=[C:4]([C:11]2[C:15]([C:16]([F:19])([F:18])[F:17])=[N:14][N:13]([C:20]3[N:25]=[CH:24][CH:23]=[CH:22][N:21]=3)[C:12]=2[NH:26][P:29]([O:34][CH2:35][CH3:36])([O:31][CH2:32][CH3:33])=[O:30])[CH:5]=[C:6]([C:16]([F:19])([F:18])[F:17])[CH:7]=1

Participants

6

Reactant 3

HCID 13139Diethyl chlorophosphateHCID 24758Sodium hydrideHCID 900100644-(7-Chloro-1,3-benzodioxol-5-yl)-2-pyrimidin-2-yl-5-(trifluoromethyl)pyrazol-3-amine

Product 1

HCID 721896474-[3-chloro-5-(trifluoromethyl)phenyl]-N-diethoxyphosphoryl-2-pyrimidin-2-yl-5-(trifluoromethyl)pyrazol-3-amineYield 23%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of 4-(7-chloro-1,3-benzodioxol-5-yl)-2-pyrimidin-2-yl-5-(trifluoromethyl)pyrazol-3-amine (0.766 g, 2.00 mmol) and NaH (0.054 g, 2.20 mmol) in tetrahydrofuran at 0° C. is added diethyl chlorophosphate (0.414 g, 2.40 mmol). The mixture is allowed to reach room temperature (20-25° C.) and further stirred for 12 hours. The reaction was diluted with water and extracted with ethyl acetate; the organic layer separated and further washed with water and then dried and concentrated. The residue was re-crystallized with a mixture of ethyl acetate and petrole ether to give the title compound (125 mg; 12%).

Workup

  1. customto reach room temperature
  2. custom(20-25° C.)
  3. extractionextracted with ethyl acetate
  4. customthe organic layer separated
  5. washfurther washed with water
  6. customdried
  7. concentrationconcentrated
  8. customThe residue was re-crystallized with a mixture of ethyl acetate and petrole ether

Sources & evidence

ORD record
ord-df0409b2864a4bf3afccdb0552921cec
Source dataset
uspto-grants-2015_11
Patent number
US09174967B2

Reaction notes

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