Peracetic Acid → HCID 67071805, compound

HRID 1260524Notes

Reaction equation

HRID 1260524 reaction equation
Br[C:2]1[CH:3]=[N:4][C:5]([O:8][C:9]2[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][CH:17]([NH:19][C:20](=[O:22])[CH3:21])[CH3:18])=[CH:11][CH:10]=2)=[N:6][CH:7]=1.C([Li])CCC.B(OC)(OC)[O:29]C.C(OO)(=O)C.S([O-])(O)=O.[Na+]>C1COCC1>[OH:29][C:2]1[CH:3]=[N:4][C:5]([O:8][C:9]2[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][CH:17]([NH:19][C:20](=[O:22])[CH3:21])[CH3:18])=[CH:11][CH:10]=2)=[N:6][CH:7]=1

Participants

7

Reactant 5

HCID 6585Peracetic AcidHCID 8470Trimethyl borateHCID 23665763Sodium BisulfiteHCID 67302547HCID 67302547, compoundHCID 178418339Butyllithium

Product 1

HCID 67071805HCID 67071805, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

N-{3-[4-(5-Bromopyrimidin-2-yloxy)phenyl]-1-methylpropyl}acetamide (509 mg, 1.397 mmol) were dissolved in 5 ml of THF and, at −78° C., n-butyllithium (1.6 M in hexane, 2.18 ml, 3.49 mmol) was added dropwise. This was followed after 20 min by addition of trimethyl borate (0.25 ml, 2.26 mmol), stirring at −78° C. for 2 h and then addition of peracetic acid (35 percent strength, 0.475 ml, 2.26 mmol) and stirring for 10 min. The reaction mixture was warmed to 0° C., stirred for 1 h and hydrolyzed at −10° C. with 5 ml of 10 percent strength sodium hydrogen sulfite solution. The solvent was removed in a rotary evaporator, the aqueous phase was extracted with ethyl acetate, the organic phase was washed with sodium chloride solution, and dried with magnesium sulfate and concentrated. The crude product was purified by preparative HPLC (PR18, acetonitrile/water 0.1% TFA). Yield: 129 mg, M+H+: 302.15. Fraction contains the desired substance only partially.

Workup

  1. stirringstirring for 10 min
  2. temperatureThe reaction mixture was warmed to 0° C.
  3. customThe solvent was removed in a rotary evaporator
  4. extractionthe aqueous phase was extracted with ethyl acetate
  5. washthe organic phase was washed with sodium chloride solution
  6. dry with materialdried with magnesium sulfate
  7. concentrationconcentrated
  8. customThe crude product was purified by preparative HPLC (PR18, acetonitrile/water 0.1% TFA)

Sources & evidence

ORD record
ord-3cd59cd8b7af4651adb45a03fd1b4e90
Source dataset
uspto-grants-2013_06
Patent number
US08470841B2

Reaction notes

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