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Triethylamine → 2-((1-ethyl-5-(pyrrolidin-1-yl)-1H-1,2,4-triazol-3-yl)ethynyl)-5,8-dimethyl-[1,2,4]triazolo[1,5-a]pyrazine

HRID 1054982
ノート
印刷プレビュー

反応式

HRID 1054982 の反応式
[CH2:1]([N:3]1[C:7]([N:8]2[CH2:12][CH2:11][CH2:10][CH2:9]2)=[N:6][C:5]([C:13]#[CH:14])=[N:4]1)[CH3:2].Br[C:16]1[N:26]=[C:19]2[C:20]([CH3:25])=[N:21][CH:22]=[C:23]([CH3:24])[N:18]2[N:17]=1.C(N(CC)CC)C>O1CCOCC1.[Cu]I.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH2:1]([N:3]1[C:7]([N:8]2[CH2:12][CH2:11][CH2:10][CH2:9]2)=[N:6][C:5]([C:13]#[C:14][C:16]2[N:26]=[C:19]3[C:20]([CH3:25])=[N:21][CH:22]=[C:23]([CH3:24])[N:18]3[N:17]=2)=[N:4]1)[CH3:2]
参加物実験手順後処理出典と根拠反応ノート

参加物

8

反応物 3

HCID 8471TriethylamineHCID 900168721-ethyl-3-ethynyl-5-pyrrolidin-1-yl-1H-[1,2,4]triazoleHCID 900257482-Bromo-5,8-dimethyl-[1,2,4]triazolo[1,5-a]pyrazine

生成物 1

HCID 727050902-((1-ethyl-5-(pyrrolidin-1-yl)-1H-1,2,4-triazol-3-yl)ethynyl)-5,8-dimethyl-[1,2,4]triazolo[1,5-a]pyrazine収率 37.2%

試薬・触媒・溶媒 4

HCID 11776
Triphenylphosphine
触媒
HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒
HCID 178418476HCID 178418476、化合物触媒
HCID 312751,4-Dioxane溶媒

実験手順

A mixture of 1-ethyl-3-ethynyl-5-(pyrrolidin-1-yl)-1H-1,2,4-triazole (79 mg, 415 μmol, Eq: 1.00), 2-bromo-5,8-dimethyl-[1,2,4]triazolo[1,5-a]pyrazine (104 mg, 457 μmol, Eq: 1.1) and triethylamine (63.0 mg, 86.8 μl, 623 μmol, Eq: 1.5) in dioxane (2.11 ml) was purged with argon, then copper (I) iodide (1.58 mg, 8.31 μmol, Eq: 0.02), bis(triphenylphosphine)palladium(II) chloride (5.83 mg, 8.31 μmol, Eq: 0.02) and triphenylphosphine (2.18 mg, 8.31 μmol, Eq: 0.02) were added, the vessel was capped and heated for 18 hours to 110° C. The crude material was applied on silica gel and purified by flash chromatography over a 20 g silica gel column using ethyl acetate 100% as eluent affording 2-((1-ethyl-5-(pyrrolidin-1-yl)-1H-1,2,4-triazol-3-yl)ethynyl)-5,8-dimethyl-[1,2,4]triazolo[1,5-a]pyrazine (52 mg, 37.2%) as an orange oil. MS: m/z=337.4 (M+H+)

後処理

  1. customwas purged with argon
  2. customthe vessel was capped
  3. temperatureheated for 18 hours to 110° C
  4. custompurified by flash chromatography over a 20 g silica gel column

出典と根拠

ORDレコード
ord-8cc4632c9cbc4ad994686a2d96f0394a
出典データセット
uspto-grants-2016_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09394311B2

反応ノート

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