2-氨基-5-溴-4-甲基吡啶 → 6-氨基-4-甲基-3-氰基吡啶

HRID 534777

反应方程式

HRID 534777 反应方程式
Br[C:2]1[C:3]([CH3:9])=[CH:4][C:5]([NH2:8])=[N:6][CH:7]=1.[Cu][C:11]#[N:12]>CN(C=O)C.CCOC(C)=O.O>[NH2:8][C:5]1[N:6]=[CH:7][C:2]([C:11]#[N:12])=[C:3]([CH3:9])[CH:4]=1

参与物

6

反应物 2

HCID 8176952-氨基-5-溴-4-甲基吡啶HCID 178418546HCID 178418546，化合物

产物 1

HCID 99641036-氨基-4-甲基-3-氰基吡啶收率 32%

试剂、催化剂与溶剂 3

HCID 962聚[6-[4-(4-氰基苯基)苯氧基]己基甲基丙烯酸酯]溶剂HCID 6228N,N-二甲基甲酰胺溶剂HCID 8857乙酸乙酯溶剂

反应条件

温度
200 °C

实验过程

A mixture of 5-bromo-4-methyl-2-pyridinamine (0.50 g, 2.7 mmol) and copper (I) cyanide (0.263 g, 2.9 mmol) in DMF (12 mL) was heated at 200° C. for a total of 1.75 h in a microwave reactor. The reaction mixture was diluted with EtOAc and water. The resulting thick dark precipitate was filtered off. The filtrate was extracted with EtOAc (×3) and the combined extracts were dried and concentrated to give a dark yellow solid (0.115 g). The filter cake was and washed with 1:1 DCM/MeOH (1 L) which was concentrated to give a second batch of dark yellow solid (0.047 g). The filter cake was washed with 2M NH3 in MeOH (200 mL) which was concentrated to give a dark green solid (0.533 g). These 3 batches of solids were purified by column chromatography using 0-100% EtOAc/hexane as the eluent to give the title compound as a white solid (total yield: 0.213 g). δH (CDCl3, 400 MHz) 8.28 (1H, s), 6.36 (1H, s), 4.87 (2H, br.s), 2.40 (3H, s). MS (ES): MH+ 134.1.

后处理

  1. filtrationThe resulting thick dark precipitate was filtered off
  2. extractionThe filtrate was extracted with EtOAc (×3)
  3. customthe combined extracts were dried
  4. concentrationconcentrated

来源与证据

ORD记录
ord-f652b0b0fe7d4cc4af77d713ae64d618
来源数据集
uspto-grants-2014_10
专利号
US08853218B2

关联笔记

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