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N,N'-Dimethylethylenediamine → 3-(4-Azido-benzyl)-2-ethyl-5,7-dimethyl-pyrazolo[1,5-a]pyrimidine

HRID 403496
ノート
印刷プレビュー

反応式

HRID 403496 の反応式
Br[C:2]1[CH:21]=[CH:20][C:5]([CH2:6][C:7]2[C:8]([CH2:18][CH3:19])=[N:9][N:10]3[C:15]([CH3:16])=[CH:14][C:13]([CH3:17])=[N:12][C:11]=23)=[CH:4][CH:3]=1.[N-:22]=[N+:23]=[N-:24].[Na+].CNCCNC.O=C1O[C@H]([C@H](CO)O)C([O-])=C1O.[Na+]>C(O)C.CCOC(C)=O.[Cu]I.O>[N:22]([C:2]1[CH:21]=[CH:20][C:5]([CH2:6][C:7]2[C:8]([CH2:18][CH3:19])=[N:9][N:10]3[C:15]([CH3:16])=[CH:14][C:13]([CH3:17])=[N:12][C:11]=23)=[CH:4][CH:3]=1)=[N+:23]=[N-:24]
参加物実験手順後処理出典と根拠反応ノート

参加物

9

反応物 4

HCID 8070N,N'-DimethylethylenediamineHCID 33557Sodium AzideHCID 23667548Sodium AscorbateHCID 683789033-(4-Bromobenzyl)-2-ethyl-5,7-dimethylpyrazolo[1,5-A]pyrimidine

生成物 1

HCID 866717563-(4-Azido-benzyl)-2-ethyl-5,7-dimethyl-pyrazolo[1,5-a]pyrimidine

試薬・触媒・溶媒 4

HCID 24350
Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)
触媒
HCID 702Ethanol溶媒
HCID 962Water溶媒
HCID 8857Ethyl Acetate溶媒

実験手順

A vial containing 3-(4-bromo-benzyl)-2-ethyl-5,7-dimethyl-pyrazolo[1,5-a]pyrimidine (3) (10 g, 29.0 mmol), sodium azide (3.78 g, 58.1 mmol), copper(I) iodide (0.553 g, 2.90 mmol), N,N′-dimethylethylenediamine (0.469 ml, 4.36 mmol) and sodium ascorbate (0.288 g, 1.452 mmol) in ethanol (45 ml)/water (15.00 ml) was submitted to microwave irradiations for 1 h at 100° C. The reaction was diluted with EtOAc and washed with sat aqu Na2 CO3, water and brine. The organic layer was dried over anhydrous Na2 SO4, filtered and concentrated under HV. The crude product was purified by flash chromatography (silica gel, EtOAc/heptane 5% to 40%) to give a pale yellow solid.

後処理

  1. customfor 1 h
  2. customat 100° C
  3. washwashed
  4. customThe organic layer was dried over anhydrous Na2 SO4
  5. filtrationfiltered
  6. concentrationconcentrated under HV
  7. customThe crude product was purified by flash chromatography (silica gel, EtOAc/heptane 5% to 40%)
  8. customto give a pale yellow solid

出典と根拠

ORDレコード
ord-480f73c0cac34404a448a6deca0b8c2c
出典データセット
uspto-grants-2014_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08748435B2

反応ノート

読み込み中…

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