4-Toluenesulfonyl chloride → 4-Methoxy-7-[(4-methylphenyl)sulfonyl]-7H-pyrrolo[2,3-d]pyrimidine

HRID 854384노트

반응식

HRID 854384 반응식
[CH3:1][O:2][C:3]1[C:4]2[CH:11]=[CH:10][NH:9][C:5]=2[N:6]=[CH:7][N:8]=1.[C:12]1([CH3:22])[CH:17]=[CH:16][C:15]([S:18](Cl)(=[O:20])=[O:19])=[CH:14][CH:13]=1.[OH-].[Na+]>C1(C)C=CC=CC=1.O.S([O-])([O-])(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.C([N+](CCCC)(CCCC)CCCC)CCC>[CH3:1][O:2][C:3]1[C:4]2[CH:11]=[CH:10][N:9]([S:18]([C:15]3[CH:16]=[CH:17][C:12]([CH3:22])=[CH:13][CH:14]=3)(=[O:20])=[O:19])[C:5]=2[N:6]=[CH:7][N:8]=1

참가 물질

7

반응물 3

HCID 73974-Toluenesulfonyl chlorideHCID 14798Sodium HydroxideHCID 2487924-Methoxy-7h-pyrrolo[2,3-d]pyrimidine

생성물 1

HCID 694318294-Methoxy-7-[(4-methylphenyl)sulfonyl]-7H-pyrrolo[2,3-d]pyrimidine수율 91.4%

시약·촉매·용매 3

HCID 11433187Bis(tetrabutylammonium) sulphate촉매HCID 962Water용매HCID 1140Toluene용매

실험 절차

A solution of 4-methoxy-7H-pyrrolo[2,3-d]pyrimidine [1.2 g, Reference Example 8] and para-toluene sulfonylchloride (1.77 g) in toluene (60 mL) was treated with a solution of sodium hydroxide (3.2 g) in water (30 mL), and tetrabutyl ammonium sulfate (27 mg). The solution was stirred vigorously at room temperature for 4 hours and partitioned between ethyl acetate and brine. The organic phase was separated, then dried over magnesium sulfate and then evaporated under reduced pressure. The residue was subjected to flash column chromatography on silica eluting with a gradient of ethyl acetate and cyclohexane (50:50 to 80:20, v/v) to give the title compound (2.23 g) as an amorphous solid. MS: 304 [MH]+. LCMS (Method B) RT=3.88 minutes.

후처리

  1. custompartitioned between ethyl acetate and brine
  2. customThe organic phase was separated
  3. dry with materialdried over magnesium sulfate
  4. customevaporated under reduced pressure

출처 및 근거

ORD 기록
ord-563eec4e7d6744de9f576d704c258940
출처 데이터셋
uspto-grants-2007_08
특허 번호
US07259154B2

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