Sodium → 2-{6-[1-(pyridin-3-yl)-1H-1,2,3-triazol-4-yl]pyridin-2-yl}pyrimidine

HRID 705033ノート

反応式

HRID 705033 の反応式
[N:1]([C:4]1[CH:5]=[N:6][CH:7]=[CH:8][CH:9]=1)=[N+:2]=[N-:3].[C:10]([C:12]1[N:17]=[C:16]([C:18]2[N:23]=[CH:22][CH:21]=[CH:20][N:19]=2)[CH:15]=[CH:14][CH:13]=1)#[CH:11].[Na].O=C1O[C@H]([C@H](CO)O)C(O)=C1O>O.C(O)(C)(C)C.O.O.O.O.O.S([O-])([O-])(=O)=O.[Cu+2]>[N:6]1[CH:7]=[CH:8][CH:9]=[C:4]([N:1]2[CH:11]=[C:10]([C:12]3[N:17]=[C:16]([C:18]4[N:23]=[CH:22][CH:21]=[CH:20][N:19]=4)[CH:15]=[CH:14][CH:13]=3)[N:3]=[N:2]2)[CH:5]=1

参加物

8

反応物 4

HCID 5360545SodiumHCID 120666873-AzidopyridineHCID 54670067L-Ascorbic AcidHCID 866981402-(6-Ethynylpyridin-2-yl)pyrimidine

生成物 1

HCID 675143582-{6-[1-(pyridin-3-yl)-1H-1,2,3-triazol-4-yl]pyridin-2-yl}pyrimidine収率 10.4%

試薬・触媒・溶媒 3

HCID 24463Copper sulfate pentahydrate触媒HCID 962Water溶媒2 回HCID 6386tert-Butanol溶媒

実験手順

100 mg (833 μmol) of 3-azidopyridine (for preparation see U.S. Pat. No. 4,775,762, CAUTION explosive!) and 151 mg (833 μmol) of 2-(6-ethynylpyridin-2-yl)pyrimidine were initially charged in a mixture of 1 ml of water and 1 ml of tert-butanol, 16.5 mg (83.3 μmol) of the sodium salt of L-ascorbic acid and 20.8 mg (83.3 μmol) of copper(II) sulfate pentahydrate were added, and the mixture was stirred at room temperature for 23 hours. The reaction mixture was then added to water and extracted repeatedly with dichloromethane. The separated organic phases were then dried over magnesium sulfate, filtered and concentrated. Chromatographic purification gave 26.0 mg (10% of theory) of 2-{6-[1-(pyridin-3-yl)-1H-1,2,3-triazol-4-yl]pyridin-2-yl}pyrimidine.

後処理

  1. additionwere added
  2. extractionextracted repeatedly with dichloromethane
  3. dry with materialThe separated organic phases were then dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customChromatographic purification

出典と根拠

ORDレコード
ord-705fe5ee5bb84c67af6bb44fce99981c
出典データセット
uspto-grants-2015_11
特許番号
US09173396B2

反応ノート

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