Trifluoroacetic acid → HCID 59224712, compound

HRID 1811744Notes

Reaction equation

HRID 1811744 reaction equation
[CH3:1][O:2][C:3](=[O:30])[C:4]1[CH:9]=[C:8]([C:10]2[CH:15]=[C:14]([S:16][CH2:17][CH2:18][NH:19]C(OC(C)(C)C)=O)[N:13]=[C:12]([NH2:27])[N:11]=2)[C:7]([CH3:28])=[CH:6][C:5]=1[CH3:29].FC(F)(F)C(O)=O>ClCCl>[CH3:1][O:2][C:3](=[O:30])[C:4]1[CH:9]=[C:8]([C:10]2[CH:15]=[C:14]([S:16][CH2:17][CH2:18][NH2:19])[N:13]=[C:12]([NH2:27])[N:11]=2)[C:7]([CH3:28])=[CH:6][C:5]=1[CH3:29]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 59224709HCID 59224709, compound

Product 1

HCID 59224712HCID 59224712, compoundYield 108.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

5-[2-Amino-6-(2-tert-butoxycarbonylaminoethylsulfanyl)pyrimidin-4-yl]-2,4-dimethylbenzoic acid methyl ester (531 mg, 1.23 mmol) obtained in Step 1 above was dissolved in dichloromethane (3.0 ml). Trifluoroacetic acid (1.5 ml) was added to the solution, and stirred at room temperature for 1 hour. The reaction solution was concentrated under reduced pressure. The resulting residue was diluted with ethyl acetate, and then a saturated aqueous sodium bicarbonate solution was added thereto. The organic layer was separated, and the aqueous layer was extracted with ethyl acetate. The organic layers were combined together, and sequentially washed with water and a saturated aqueous sodium chloride solution. The ethyl acetate solution was dried over anhydrous magnesium sulfate. After filtration, the filtrate was concentrated under reduced pressure to yield the crude product of 5-[2-amino-6-(2-aminoethylsulfanyl)pyrimidin-4-yl]-2,4-dimethylbenzoic acid methyl ester (443 mg) as a white solid material.

Workup

  1. concentrationThe reaction solution was concentrated under reduced pressure
  2. additionThe resulting residue was diluted with ethyl acetate
  3. additiona saturated aqueous sodium bicarbonate solution was added
  4. customThe organic layer was separated
  5. extractionthe aqueous layer was extracted with ethyl acetate
  6. washsequentially washed with water
  7. dry with materialThe ethyl acetate solution was dried over anhydrous magnesium sulfate
  8. filtrationAfter filtration
  9. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-22b74e1ad7fc4ea98b684bb35530ea18
Source dataset
uspto-grants-2013_01
Patent number
US08362236B2

Reaction notes

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