4-Toluenesulfonyl chloride → 2,4-dichloro-5-iodo-7-tosyl-7H-pyrrolo[2,3-d]pyrimidine

HRID 645702ノート

反応式

HRID 645702 の反応式
[Cl:1][C:2]1[N:3]=[C:4]([Cl:12])[C:5]2[C:10]([I:11])=[CH:9][NH:8][C:6]=2[N:7]=1.[C:13]1([CH3:23])[CH:18]=[CH:17][C:16]([S:19](Cl)(=[O:21])=[O:20])=[CH:15][CH:14]=1.C(N(CC)CC)C.CN(C1C=CC=CN=1)C>C(Cl)Cl>[Cl:1][C:2]1[N:3]=[C:4]([Cl:12])[C:5]2[C:10]([I:11])=[CH:9][N:8]([S:19]([C:16]3[CH:17]=[CH:18][C:13]([CH3:23])=[CH:14][CH:15]=3)(=[O:21])=[O:20])[C:6]=2[N:7]=1

参加物

6

反応物 4

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 218852-DimethylaminopyridineHCID 574159022,4-Dichloro-5-iodo-7H-pyrrolo(2,3-d)pyrimidine

生成物 1

HCID 579902932,4-dichloro-5-iodo-7-tosyl-7H-pyrrolo[2,3-d]pyrimidine収率 74.6%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a mixture of 2,4-dichloro-5-iodo-7H-pyrrolo[2,3-d]pyrimidine (1.80 g, 5.73 mmol) in CH2Cl2 (20 mL) was added p-toluenesulfonyl chloride (TsCl) (1.09 g, 5.73 mmol) and triethylamine (TEA) (1.60 mL, 11.46 mmol), followed by dimethylaminopyridine (DMAP) (70 mg, 0.573 mmol). After stirring for 1 h at room temperature, the solution was concentrated, and the residue was partitioned between ethyl acetate and H2O. The organic layer was separated, washed sequentially with 1N HCl and 5% NaHCO3. The organic extracts were dried over Na2SO4 and concentrated to give 2,4-dichloro-5-iodo-7-tosyl-7H-pyrrolo[2,3-d]pyrimidine (2.0 g).

後処理

  1. concentrationthe solution was concentrated
  2. customthe residue was partitioned between ethyl acetate and H2O
  3. customThe organic layer was separated
  4. washwashed sequentially with 1N HCl and 5% NaHCO3
  5. dry with materialThe organic extracts were dried over Na2SO4
  6. concentrationconcentrated

出典と根拠

ORDレコード
ord-a9c98a259f1e4c489f40a0faf2001401
出典データセット
uspto-grants-2010_04
特許番号
US07705004B2

反応ノート

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