Potassium Carbonate → Trifluoroacetic acid

HRID 2207429Notes

Reaction equation

HRID 2207429 reaction equation
[N+](=[C:3](P(=O)(OC)OC)C(=O)C)=[N-].[CH3:13][C:14]1[CH:15]=[C:16]([C:31]2[CH:32]=[CH:33][C:34]([CH:37]=O)=[N:35][CH:36]=2)[CH:17]=[C:18]([NH:20][C:21]2[N:26]=[C:25]([C:27]([F:30])([F:29])[F:28])[CH:24]=[CH:23][N:22]=2)[CH:19]=1.[C:39](=[O:42])([O-])[O-:40].[K+].[K+]>CO.O>[C:37]([C:34]1[N:35]=[CH:36][C:31]([C:16]2[CH:17]=[C:18]([NH:20][C:21]3[N:26]=[C:25]([C:27]([F:28])([F:29])[F:30])[CH:24]=[CH:23][N:22]=3)[CH:19]=[C:14]([CH3:13])[CH:15]=2)=[CH:32][CH:33]=1)#[CH:3].[C:39]([OH:40])([C:27]([F:30])([F:29])[F:28])=[O:42]

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 131735917HCID 131735917, compoundHCID 136023029(1E)-1-diazo-1-dimethoxyphosphorylpropan-2-one

Product 2

HCID 6422Trifluoroacetic acidHCID 131735920HCID 131735920, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

Dimethyl (1-diazo-2-oxopropyl)phosphonate (0.200 mL, 1.15 mmol) was added to a solution of 5-(3-methyl-5-{[4-(trifluoromethyl)pyrimidin-2-yl]amino}phenyl)pyridine-2-carbaldehyde (201 mg, 0.560 mmol) and potassium carbonate (155 mg, 1.12 mmol) in dry methanol (8.00 mL). The mixture was stirred at room temperature for 2 hours. The mixture was diluted with water and extracted with ethyl acetate. The organic layer was concentrated under reduced pressure and the residue was directly purified by reverse phase HPLC to yield N-[3-(6-ethynylpyridin-3-yl)-5-methylphenyl]-4-(trifluoromethyl)pyrimidin-2-amine as a TFA salt. MS APCI C19H14F3N4 [M+H]+ 355. found 355.

Workup

  1. extractionextracted with ethyl acetate
  2. concentrationThe organic layer was concentrated under reduced pressure
  3. customthe residue was directly purified by reverse phase HPLC

Sources & evidence

ORD record
ord-2f08cf2d4d444ed39ce4ae4fac3d5a62
Source dataset
uspto-grants-2016_06
Patent number
US09376418B2

Reaction notes

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