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

HRID 2072783Notes

Reaction equation

HRID 2072783 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 90 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 90 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-90eebc4ad4e847a59f2b2c908d02e590
Source dataset
uspto-grants-1990_04
Patent number
US04914203

Reaction notes

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