Trifluoroacetic acid → HCID 70926821, compound

HRID 240486Notes

Reaction equation

HRID 240486 reaction equation
C(OC([N:8]1[C:12]([CH3:14])([CH3:13])[CH2:11][C:10](=[O:15])[N:9]1[C:16]1[N:21]=[CH:20][C:19]([C:22]#[C:23][C:24]2[CH:29]=[CH:28][CH:27]=[C:26]([F:30])[CH:25]=2)=[CH:18][N:17]=1)=O)(C)(C)C.C(O)(C(F)(F)F)=O>ClCCl>[F:30][C:26]1[CH:25]=[C:24]([C:23]#[C:22][C:19]2[CH:20]=[N:21][C:16]([N:9]3[C:10](=[O:15])[CH2:11][C:12]([CH3:14])([CH3:13])[NH:8]3)=[N:17][CH:18]=2)[CH:29]=[CH:28][CH:27]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 70926797HCID 70926797, compound

Product 1

HCID 70926821HCID 70926821, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(118 mg, 0.29 mmol) 2-[5-(3-Fluoro-phenylethynyl)-pyrimidin-2-yl]-5,5-dimethyl-3-oxo-pyrazolidine-1-carboxylic acid tert-butyl ester (Example 15, step 3) was dissolved in dichloromethane (2 ml) and TFA (0.55 ml, 7.2 mmol, 25 equiv.) was added at room temperature and stirred for 16 hours. The reaction mixture was extracted with saturated Na2CO3 solution and a small amount of dichloromethane. The organic extract was loaded directly to a silica gel column. The crude product was purified by flash chromatography on a silica gel column eluting with an ethyl acetate:heptane gradient 0:100 to 100:0. The desired 2-[5-(3-fluoro-phenylethynyl)-pyrimidin-2-yl]-5,5-dimethyl-pyrazolidin-3-one (61 mg, 69% yield) was obtained as a light yellow solid, MS: m/e=311.2 (M+H+).

Workup

  1. extractionThe reaction mixture was extracted with saturated Na2CO3 solution
  2. extractionThe organic extract
  3. customThe crude product was purified by flash chromatography on a silica gel column
  4. washeluting with an ethyl acetate

Sources & evidence

ORD record
ord-8ffb07500f18414f89c35d0efe1b3846
Source dataset
uspto-grants-2014_02
Patent number
US08648088B2

Reaction notes

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