二溴三苯基膦 → 5-Bromo-3-(5-phenyl-1,3,4-thiadiazol-2-yl)pyrazin-2-amine

HRID 78593

反应方程式

HRID 78593 反应方程式
[NH2:1][C:2]1[C:3]([C:9](O)=O)=[N:4][C:5]([Br:8])=[CH:6][N:7]=1.[C:12]1([C:18](=[S:21])[NH:19][NH2:20])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.BrP(Br)(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.CCN(C(C)C)C(C)C>C(#N)C>[Br:8][C:5]1[N:4]=[C:3]([C:9]2[S:21][C:18]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)=[N:19][N:20]=2)[C:2]([NH2:1])=[N:7][CH:6]=1

参与物

6

反应物 4

HCID 70579二溴三苯基膦HCID 81531N,N-二异丙基乙胺HCID 3361911Benzenecarbothioic acid, hydrazideHCID 185216003-氨基-6-溴吡嗪-2-甲酸

产物 1

HCID 594718915-Bromo-3-(5-phenyl-1,3,4-thiadiazol-2-yl)pyrazin-2-amine收率 43%

试剂、催化剂与溶剂 1

HCID 6342乙腈溶剂

实验过程

3-amino-6-bromo-pyrazine-2-carboxylic acid (1.000 g, 4.588 mmol) and benzenecarbothiohydrazide (759.1 mg, 4.588 mmol) were suspended in acetonitrile (25.00 mL), cooled in an ice bath and then treated with dibromo-triphenyl-phosphorane (4.453 g, 10.55 mmol) The reaction mixture was allowed to stir in an ice bath for 2 hours and then DIPEA (1.778 g, 2.396 mL, 13.76 mmol) was added slowly at 10° C. The reaction was left to stir at 0-10° C. for a further hour and the resultant precipitate was isolated by filtration, washed with a small amount of acetonitrile and dried (659 mg, 43% Yield). MS (ES+) 335.93

后处理

  1. temperaturecooled in an ice bath
  2. waitThe reaction was left
  3. stirringto stir at 0-10° C. for a further hour

来源与证据

ORD记录
ord-87db2c5641a543e298f4bac069230a5a
来源数据集
uspto-grants-2014_09
专利号
US08841308B2

关联笔记

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