Hydrochloric Acid → HCID 68165145, compound

HRID 921290Notes

Reaction equation

HRID 921290 reaction equation
Cl[C:2]1[C:7]([C:8]([F:11])([F:10])[F:9])=[CH:6][N:5]=[C:4]([NH:12][C:13]2[CH:18]=[CH:17][C:16]([P:19]([CH3:22])([CH3:21])=[O:20])=[CH:15][CH:14]=2)[N:3]=1.Cl.[CH3:24][C:25]1[CH:26]=[C:27]([CH:29]=[C:30]([CH3:32])[CH:31]=1)[NH2:28]>C(O)C.CO>[CH3:24][C:25]1[CH:26]=[C:27]([NH:28][C:2]2[C:7]([C:8]([F:11])([F:10])[F:9])=[CH:6][N:5]=[C:4]([NH:12][C:13]3[CH:18]=[CH:17][C:16]([P:19]([CH3:22])([CH3:21])=[O:20])=[CH:15][CH:14]=3)[N:3]=2)[CH:29]=[C:30]([CH3:32])[CH:31]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 79493,5-DimethylanilineHCID 86668788HCID 86668788, compound

Product 1

HCID 68165145HCID 68165145, compoundYield 65%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 887MethanolSolvent

Procedure

To a solution of 4-chloro-N-[4-(dimethylphosphoryl)phenyl]-5-(trifluoromethyl)pyrimidin-2-amine (prepared as in Example 1: 40 mg, 0.12 mmol) in 2 mL of ethanol was added 10 L of Hydrochloric acid in Methanol (2M) and 3,5-Dimethyl aniline (14 mg, 0.12 mmol). The mixture was microwave at 120 degrees for 20 minutes. The reaction mixture was filtered through a syringe filter and purified by prep-HPLC (Waters Sunfire C18 column with ACN/water mobile phases) to yield a white solid as product (32 mg, 65% yield.) MS/ES+: m/z=435

Workup

  1. customat 120 degrees
  2. customfor 20 minutes
  3. filtrationThe reaction mixture was filtered through a syringe
  4. filtrationfilter
  5. custompurified by prep-HPLC (Waters Sunfire C18 column with ACN/water mobile phases)
  6. customto yield a white solid as product (32 mg, 65% yield.) MS/ES+

Sources & evidence

ORD record
ord-b754dfb9aa654ae4b720f3ff0982f9fa
Source dataset
uspto-grants-2016_03
Patent number
US09273077B2

Reaction notes

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