Water → HCID 11579342, compound

HRID 576705Notes

Reaction equation

HRID 576705 reaction equation
[F:1][C:2]([F:13])([F:12])[C:3]1[CH:8]=[CH:7][N:6]=[C:5]([C:9]([OH:11])=[O:10])[N:4]=1.[CH3:14][Si](C=[N+]=[N-])(C)C.O>C1COCC1.CO.CC(O)=O>[F:13][C:2]([F:1])([F:12])[C:3]1[CH:8]=[CH:7][N:6]=[C:5]([C:9]([O:11][CH3:14])=[O:10])[N:4]=1

Participants

7

Reactant 3

HCID 962WaterHCID 167693TrimethylsilyldiazomethaneHCID 253241464-(Trifluoromethyl)pyrimidine-2-carboxylic acid

Product 1

HCID 11579342HCID 11579342, compound

Reagents, catalysts & solvents 3

HCID 176Acetic AcidCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

4-(trifluoromethyl)pyrimidine-2-carboxylic acid (500 mg, 2.6 mmol) was dissolved in a mixture of 1 mL of THF and 300 μL of MeOH and cooled to 0° C. Trimethylsilyldiazomethane (2M in ether, 2.6 mL, 5.2 mmol) was added dropwise. The solution was stirred for 2 hours at 0° C., then 1 hour at rt. A few drops of AcOH were added, followed by water. The aqueous solution was extracted three times with EtOAc. The combined organic layers were dried (Na2SO4), filtered, and concentrated to give an oil which was used without further purification. MS (ESI): mass calcd. for C7H5F3N2O2, 206.0; m/z found, 207.0 [M+H]+. 1H NMR (400 MHz, CDCl3) δ 9.24 (d, J=5.0 Hz, 1H), 7.87 (d, J=5.0 Hz, 1H), 4.10 (s, 3H).

Workup

  1. custom1 hour
  2. customat rt
  3. extractionThe aqueous solution was extracted three times with EtOAc
  4. dry with materialThe combined organic layers were dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto give an oil which
  8. customwas used without further purification

Sources & evidence

ORD record
ord-2ecd3e9a2eb5413a89c3927d256f4a34
Source dataset
uspto-grants-2015_05
Patent number
US09040534B2

Reaction notes

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