碘 → 7-(苯磺酰基)-4-氯-6-碘-7H-吡咯并[2,3-D]嘧啶

HRID 2375813笔记

反应方程式

HRID 2375813 反应方程式
[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

参与物

7

反应物 4

HCID 807碘HCID 962聚[6-[4-(4-氰基苯基)苯氧基]己基甲基丙烯酸酯]HCID 2724682二异丙基氨基锂HCID 109463064-氯-7-(苯基磺酰基)-7h-吡咯并[2,3-d]嘧啶

产物 1

HCID 574158857-(苯磺酰基)-4-氯-6-碘-7H-吡咯并[2,3-D]嘧啶

试剂、催化剂与溶剂 2

HCID 6344二氯甲烷溶剂HCID 8028四氢呋喃溶剂2 次

实验过程

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).

后处理

  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

来源与证据

ORD记录
ord-c84059d700734fa6a06040b6d5a800d8
来源数据集
uspto-grants-2008_12
专利号
US07465726B2

反应笔记

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