Trifluoroacetic acid → HCID 22636832, compound

HRID 2416297Notes

Reaction equation

HRID 2416297 reaction equation
[CH2:1]([O:3][C:4]1[CH:9]=[C:8]([CH2:10][C:11]2[C:12]([NH2:18])=[N:13][C:14]([NH2:17])=[N:15][CH:16]=2)[CH:7]=[C:6]([O:19][CH2:20][CH3:21])[C:5]=1[C:22]1[CH:27]=[CH:26][C:25](SC)=[CH:24][CH:23]=1)[CH3:2].F[C:31](F)(F)C(O)=O.ClC1C=CC=C(C(OO)=O)C=1.[O-:48][S:49]([O-:52])(=S)=O.[Na+].[Na+]>C(Cl)Cl>[CH2:1]([O:3][C:4]1[CH:9]=[C:8]([CH2:10][C:11]2[C:12]([NH2:18])=[N:13][C:14]([NH2:17])=[N:15][CH:16]=2)[CH:7]=[C:6]([O:19][CH2:20][CH3:21])[C:5]=1[C:22]1[CH:23]=[CH:24][C:25]([S:49]([CH3:31])(=[O:52])=[O:48])=[CH:26][CH:27]=1)[CH3:2]

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 24477Sodium ThiosulfateHCID 70297m-Chloroperbenzoic acidHCID 22636907HCID 22636907, compound

Product 1

HCID 22636832HCID 22636832, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

5-(2,6-Diethoxy-4′-methylsulphanyl-biphenyl-4-ylmethyl)-pyrimidine-2,4-diamine (616 mg; 1.5 mmol) is suspended in methylene chloride (12 ml), and trifluoroacetic acid (0.276 ml; 3.6 mmol) is added. After cooling to 0° C., m-chloroperbenzoic acid (456 mg; 2.25 mmol) is added. After 40 minutes a 10% aqueous Na2S2O3 solution (15 ml) is added and the mixture is stirred at room temperature for 15 minutes. It is then extracted with methylene chloride (60 ml) and the extract is washed with an aqueous saturated sodium bicarbonate solution, dried over magnesium sulphate, filtered with suction and concentrated. The crude product is chromatographed over silica gel (100 g) with methylene chloride/methanol/NH4OH (conc.) (19/1/0.05).

Workup

  1. extractionIt is then extracted with methylene chloride (60 ml)
  2. washthe extract is washed with an aqueous saturated sodium bicarbonate solution
  3. dry with materialdried over magnesium sulphate
  4. filtrationfiltered with suction
  5. concentrationconcentrated
  6. customThe crude product is chromatographed over silica gel (100 g) with methylene chloride/methanol/NH4OH (conc.) (19/1/0.05)

Sources & evidence

ORD record
ord-7883791f38114c63a35c5096f4691d7e
Source dataset
uspto-grants-2004_11
Patent number
US06821980B1

Reaction notes

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