碘甲烷 → 6-Bromo-4-chloro-7-methyl-7H-pyrrolo[2,3-D]pyrimidine

HRID 851908笔记

反应方程式

HRID 851908 反应方程式
[Br:1][C:2]1[NH:11][C:5]2[N:6]=[CH:7][N:8]=[C:9]([Cl:10])[C:4]=2[CH:3]=1.[H-].[Na+].[CH3:14]I>C1COCC1>[Br:1][C:2]1[N:11]([CH3:14])[C:5]2[N:6]=[CH:7][N:8]=[C:9]([Cl:10])[C:4]=2[CH:3]=1

参与物

5

反应物 3

HCID 6328碘甲烷HCID 24758氢化钠HCID 457898276-溴-4-氯-7H-吡咯并嘧啶

产物 1

HCID 589283276-Bromo-4-chloro-7-methyl-7H-pyrrolo[2,3-D]pyrimidine收率 77%

试剂、催化剂与溶剂 1

HCID 8028四氢呋喃溶剂

实验过程

To a solution of 6-bromo-4-chloro-7H-pyrrolo[2,3-d]pyrimidine (122 mg, 0.53 mmol), prepared as in reference 1, in THF (5 mL) at 0° C. is added NaH (31.8 mg, 0.80 mmol, 60% dispersion in oil) portion wise and the reaction mixture is warmed to room temperature for 1 hour. Methyl iodide (103 μL, 1.59 mmol) is added and the mixture is stirred overnight. The reaction is quenched with water and extracted three times with EtOAc. The combined organic layer is washed with brine, dried over MgSO4, and concentrated. Flash column chromatography of the crude product using 1% MeOH in DCM yielded 100 mg of 6-bromo-4-chloro-7-methyl-7H-pyrrolo[2,3-d]pyrimidine (77%); 1H NMR (500 MHz, DMSO) δ 8.64 (s, 1H), 6.96 (s, 1H), 3.79 (s, 3H); LC-ESMS observed [M+H]+ 245.9 (calculated for C7H5BrClN3 244.9).

后处理

  1. customThe reaction is quenched with water
  2. extractionextracted three times with EtOAc
  3. washThe combined organic layer is washed with brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated

来源与证据

ORD记录
ord-d46715d983734042aa618886ba717c99
来源数据集
uspto-grants-2007_08
专利号
US07253166B2

反应笔记

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