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Butyl iodide → 3-(4-Bromo-2-butyl-thiazol-5-yl)-7-(1-ethyl-propyl)-2,5-dimethyl-pyrazolo[1,5-a]pyrimidine

HRID 1660750
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HRID 1660750 반응식
[CH2:1]([Li])[CH2:2][CH2:3][CH3:4].Br[C:7]1[S:8][C:9]([C:13]2[C:14]([CH3:28])=[N:15][N:16]3[C:21]([CH:22]([CH2:25][CH3:26])[CH2:23][CH3:24])=[CH:20][C:19]([CH3:27])=[N:18][C:17]=23)=[C:10]([Br:12])[N:11]=1.ICCCC.[Cl-].N>C1COCC1>[Br:12][C:10]1[N:11]=[C:7]([CH2:1][CH2:2][CH2:3][CH3:4])[S:8][C:9]=1[C:13]1[C:14]([CH3:28])=[N:15][N:16]2[C:21]([CH:22]([CH2:25][CH3:26])[CH2:23][CH3:24])=[CH:20][C:19]([CH3:27])=[N:18][C:17]=12
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 10962Butyl iodideHCID 20976574Ammonia chlorideHCID 674295502,4-Dibromo-5-(2,5-dimethyl-7-(pentan-3-yl)pyrazolo[1,5-a]pyrimidin-3-yl)thiazoleHCID 178418339Butyllithium

생성물 1

HCID 674291383-(4-Bromo-2-butyl-thiazol-5-yl)-7-(1-ethyl-propyl)-2,5-dimethyl-pyrazolo[1,5-a]pyrimidine수율 35.8%

시약·촉매·용매 1

HCID 8028
Tetrahydrofuran
용매

실험 절차

Under a nitrogen atmosphere, add n-butyl lithium (2.5 M in hexane, 0.2 mL, 0.5 mmol) to a solution of 3-(2,4-dibromo-thiazol-5-yl)-7-(1-ethyl-propyl)-2,5-dimethyl-pyrazolo[1,5-a]pyrimidine (230 mg, 0.5 mmol) in THF (3 mL) at −78° C. After 30 min, add 1-iodobutane (138 mg, 0.75 mmol) and continue stirring for 1 hour. Warm up to room temperature and stir for one hour. Quench the reaction by adding saturated ammonia chloride solution and extract with ethyl acetate. Dry the organic portion over sodium sulfate, filter, and concentrate to a residue. Purify the crude material by flash chromatography, eluting with hexanes/ethyl acetate (10/1.5) to give the title compound as orange foam (78 mg). ES/MS m/z (81Br) 437.4 (M+1)+.

후처리

  1. stirringstir for one hour
  2. customQuench
  3. customthe reaction
  4. extractionextract with ethyl acetate
  5. dry with materialDry the organic portion over sodium sulfate
  6. filtrationfilter
  7. concentrationconcentrate to a residue
  8. customPurify the crude material by flash chromatography
  9. washeluting with hexanes/ethyl acetate (10/1.5)

출처 및 근거

ORD 기록
ord-8c52398663134741991bc5c084220cbd
출처 데이터셋
uspto-grants-2011_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08030304B2

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