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

HRID 1721868노트

반응식

HRID 1721868 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-750466eeec1446298c08f1d0fcea07c9
출처 데이터셋
uspto-grants-1989_08
특허 번호
US04853389

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