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

HRID 403496
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HRID 403496 반응식
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]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

9

반응물 4

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

생성물 1

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

시약·촉매·용매 4

HCID 24350
Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)
촉매
HCID 702Ethanol용매
HCID 962Water용매
HCID 8857Ethyl Acetate용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-480f73c0cac34404a448a6deca0b8c2c
출처 데이터셋
uspto-grants-2014_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08748435B2

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