1H-1,2,4-Triazole → 4-Chloro-6-(1H-1,2,4-triazol-1-yl)pyrimidine

HRID 1876051ノート

反応式

HRID 1876051 の反応式
Cl[C:2]1[CH:7]=[C:6]([Cl:8])[N:5]=[CH:4][N:3]=1.[NH:9]1[CH:13]=[N:12][CH:11]=[N:10]1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C.O>[Cl:8][C:6]1[CH:7]=[C:2]([N:9]2[CH:13]=[N:12][CH:11]=[N:10]2)[N:3]=[CH:4][N:5]=1

参加物

6

反応物 3

HCID 92571H-1,2,4-TriazoleHCID 10796Cesium carbonateHCID 709434,6-Dichloropyrimidine

生成物 1

HCID 190236504-Chloro-6-(1H-1,2,4-triazol-1-yl)pyrimidine収率 76.5%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

A mixture of 4,6-dichloropyrimidine (5.96 g, 40 mmol), 1H-1,2,4-triazole (1.381 g, 20.00 mmol), and cesium carbonate (13.03 g, 40.0 mmol) was stirred in DMF (25 mL) at room temperature for 16 h. The reaction was diluted with 100 mL water and extracted with EtOAc. The combined organic extracts were concentrated and purified by flash chromatography on a 160 g silica gel cartridge with 25 to 50% EtOAc in hexane to yield 4-chloro-6-(1H-1,2,4-triazol-1-yl)pyrimidine (2.78 g, 38% yield). 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 9.21 (1H, s), 8.87 (1H, s), 8.15 (1H, s), 7.91 (1H, s). LCMS: RT=0.68 min, MH+=182.1.

後処理

  1. extractionextracted with EtOAc
  2. concentrationThe combined organic extracts were concentrated
  3. custompurified by flash chromatography on a 160 g silica gel cartridge with 25 to 50% EtOAc in hexane

出典と根拠

ORDレコード
ord-6f95e84cce954314aa97a9b537d6a185
出典データセット
uspto-grants-2012_11
特許番号
US08309577B2

反応ノート

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