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

HRID 854384ノート

反応式

HRID 854384 の反応式
[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

参加物

7

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 11433187Bis(tetrabutylammonium) sulphate触媒HCID 962Water溶媒HCID 1140Toluene溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-563eec4e7d6744de9f576d704c258940
出典データセット
uspto-grants-2007_08
特許番号
US07259154B2

反応ノート

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