m-Chloroperbenzoic acid → N-[[(1-Methylethyl)amino]carbonyl]-4-(methylsulfinyl)-2-amino-5-pyrimidinesulfonamide

HRID 1721868Notes

Reaction equation

HRID 1721868 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([S:8][CH3:9])[C:5]([S:10]([NH:13][C:14]([NH:16][CH:17]([CH3:19])[CH3:18])=[O:15])(=[O:12])=[O:11])=[CH:4][N:3]=1.[Na].C(C1C=CC=CC=1)(=[O:28])C1C=CC=CC=1.ClC1C=CC=C(C(OO)=O)C=1>C1COCC1>[CH3:18][CH:17]([NH:16][C:14]([NH:13][S:10]([C:5]1[C:6]([S:8]([CH3:9])=[O:28])=[N:7][C:2]([NH2:1])=[N:3][CH:4]=1)(=[O:12])=[O:11])=[O:15])[CH3:19]

Participants

5

Reactant 3

HCID 70297m-Chloroperbenzoic acidHCID 198603812-Amino-N-[[(1-methylethyl)amino]carbonyl]-4-(methylthio)-5-pyrimidinesulfonamideHCID 66591377Sodium benzophenone

Product 1

HCID 19860380N-[[(1-Methylethyl)amino]carbonyl]-4-(methylsulfinyl)-2-amino-5-pyrimidinesulfonamideYield 84%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-Amino-N-[[(1-methylethyl)amino]carbonyl]-4-(methylthio)-5-pyrimidinesulfonamide (3.0 g, 9.84 mmol) was dissolved in dry (freshly distilled from sodium/benzophenone) THF (60 mL) and m-chloroperbenzoic acid (MCPBA) (2.55 g, 11.81 mmol, 80% 1.2 eq) was added as a solid. The reaction turned yellow and a white solid precipitated out of solution. After 30 minutes the reaction was diluted with ethyl ether (60 mL) and the white solid was filtered, washed with THF, then with ether three times and air dried for 2 hours, to yield 2.64 g (8.22 mmol, 84%) of product, m.p. 140° C.(dec.). The product was unstable to heat but could be stored under nitrogen in the freezer for weeks.

Workup

  1. customin dry (
  2. additionwas added as a solid
  3. customa white solid precipitated out of solution
  4. additionAfter 30 minutes the reaction was diluted with ethyl ether (60 mL)
  5. filtrationthe white solid was filtered
  6. washwashed with THF
  7. dry with materialwith ether three times and air dried for 2 hours

Sources & evidence

ORD record
ord-750466eeec1446298c08f1d0fcea07c9
Source dataset
uspto-grants-1989_08
Patent number
US04853389

Reaction notes

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