Methyl iodide → 7-(Benzenesulfonyl)-4-chloro-6-methyl-7H-pyrrolo[2,3-d]pyrimidine

HRID 409137ノート

反応式

HRID 409137 の反応式
[Cl:1][C:2]1[C:3]2[CH:10]=[CH:9][N:8]([S:11]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)(=[O:13])=[O:12])[C:4]=2[N:5]=[CH:6][N:7]=1.[CH3:20]N(CCN(C)C)C.[Li]CCCC.CI>C1COCC1>[Cl:1][C:2]1[C:3]2[CH:10]=[C:9]([CH3:20])[N:8]([S:11]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)(=[O:13])=[O:12])[C:4]=2[N:5]=[CH:6][N:7]=1

参加物

6

反応物 4

HCID 6328Methyl iodideHCID 8037N,N,N',N'-TetramethylethylenediamineHCID 109463064-Chloro-7-(phenylsulfonyl)-7H-pyrrolo[2,3-D]pyrimidineHCID 178418339Butyllithium

生成物 1

HCID 224844987-(Benzenesulfonyl)-4-chloro-6-methyl-7H-pyrrolo[2,3-d]pyrimidine

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To the solution of 4-chloro-7-(phenylsulfonyl)-7H-pyrrolo[2,3-d]pyrimidine (3 g, 12.6 mmol, 1.0 eq) and TMEDA (3.0 mL, 18.9 mmol, 1.5 eq) in THF (120 mL), n-BuLi (7.5 mL, 18.9 mmol, 1.5 eq) was added at −78° C. After 3 min, CH3I (3.7 mL, 59.2 mmol, 4.7 eq) was added. After 3 h, the reaction mixture was warmed to RT over 1 h. The reaction was quenched by addition of sat NH4Cl (10 mL) at −78° C. EtOAc (200 mL) and water (100 mL) was added. The organic layer was separated, dried and concentrated to afford 4-chloro-6-methyl-7-(phenylsulfonyl)-7H-pyrrolo[2,3-d]pyrimidine as a brown solid (6.7 g, 90% in yield).

後処理

  1. waitAfter 3 h
  2. customThe reaction was quenched by addition of sat NH4Cl (10 mL) at −78° C
  3. additionEtOAc (200 mL) and water (100 mL) was added
  4. customThe organic layer was separated
  5. customdried
  6. concentrationconcentrated
  7. customto afford

出典と根拠

ORDレコード
ord-d07268f881c2424ebdbc298135769907
出典データセット
uspto-grants-2014_06
特許番号
US08759358B1

反応ノート

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