乙酸乙酯 → 6-(1-甲基-1H-吡唑-4-基)哒嗪-3-胺

HRID 69165

反应方程式

HRID 69165 反应方程式
[NH2:1][C:2]1[N:3]=[N:4][C:5](Cl)=[CH:6][CH:7]=1.C([O-])([O-])=O.[Na+].[Na+].CCO[C:18]([CH3:20])=O>[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH3:5][N:4]1[CH:20]=[C:18]([C:5]2[N:4]=[N:3][C:2]([NH2:1])=[CH:7][CH:6]=2)[CH:2]=[N:3]1

参与物

5

反应物 3

HCID 8857乙酸乙酯HCID 10340Carbonic acid sodium salt (1:2)HCID 216433-氨基-6-氯哒嗪

产物 1

HCID 622026836-(1-甲基-1H-吡唑-4-基)哒嗪-3-胺

试剂、催化剂与溶剂 1

HCID 11979704四三苯基膦钯催化剂

实验过程

3-Amino-6-chloropyridazine (7.76 g, 59.9 mmol) was introduced in a round bottom flask with 1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaboran-2-yl)-1H-pyrazole (13.1 g, 59.9 mmol) and dissolved in 2-dimethoxyethane (160 mL). An aqueous solution of 2 M Na2CO3 (110 mL, 220 mmol) was added to this mixture and also tetrakis-(triphenylphosphine)-palladium (3.5 g, 2.99 mmol). The RM was refluxed for 26 h under nitrogen. Then was taken up with EtOAc and washed with 1N NaOH and brine. The organic layer was dried over Na2SO4 and the solvent was removed. The residue was triturated with Et2O to afford the title compound as a yellow solid (tR 0.9 min (conditions 2), MH+=176).

后处理

  1. temperatureThe RM was refluxed for 26 h under nitrogen
  2. washwashed with 1N NaOH and brine
  3. dry with materialThe organic layer was dried over Na2SO4
  4. customthe solvent was removed
  5. customThe residue was triturated with Et2O

来源与证据

ORD记录
ord-838935df22194fc2983e290890e65c7f
来源数据集
uspto-grants-2014_09
专利号
US08822468B2

关联笔记

加载中…