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

HRID 1876051노트

반응식

HRID 1876051 반응식
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

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-6f95e84cce954314aa97a9b537d6a185
출처 데이터셋
uspto-grants-2012_11
특허 번호
US08309577B2

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