Iodine → 4-Chloro-6-iodo-7-phenylsulfonyl-7H-pyrrolo[2,3-D]pyrimidine

HRID 2375813ノート

反応式

HRID 2375813 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.[Li+].CC([N-]C(C)C)C.[I:28]I.O>C1COCC1.C(Cl)Cl>[Cl:1][C:2]1[C:3]2[CH:10]=[C:9]([I:28])[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

7

反応物 4

HCID 807IodineHCID 962WaterHCID 2724682Lithium diisopropylamideHCID 109463064-Chloro-7-(phenylsulfonyl)-7H-pyrrolo[2,3-D]pyrimidine

生成物 1

HCID 574158854-Chloro-6-iodo-7-phenylsulfonyl-7H-pyrrolo[2,3-D]pyrimidine

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 8028Tetrahydrofuran溶媒2 回

実験手順

To a stirred solution of 4-chloro-7-(phenylsulfonyl)-7H-pyrrolo[2,3-d]-pyrimidine (5.0 g, 0.017 mol) in THF (200 mL) under inert atmosphere, at −78° C., was added 2.0 M LDA solution (9.8 mL, 0.0195 mol) over a period of 15 min. After 1 h a solution of iodine (4.97 g, 0.0196 mol) in THF (50 mL) was added dropwise over a period of 15 min. The resulting solution was stirred for a further 3 h. Water (10 mL) was then added and the mixture allowed to reach r.t. The mixture was diluted with DCM (1 l), washed with brine (2×100 mL), dried and concentrated under reduced pressure. The resulting solid was triturated with MeCN to afford the 4-chloro-6-iodo-7-(phenylsulfonyl)-7H-pyrrolo[2,3-d]pyrimidine. 1H NMR (CDCl3, 400 MHz) 7.05 (1H, s), 7.50 (2H, t), 7.60 (1H, t), 8.20 (2H, d) and 8.65 (1H, br s).

後処理

  1. customto reach r.t
  2. washwashed with brine (2×100 mL)
  3. customdried
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting solid was triturated with MeCN

出典と根拠

ORDレコード
ord-c84059d700734fa6a06040b6d5a800d8
出典データセット
uspto-grants-2008_12
特許番号
US07465726B2

反応ノート

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