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Tributyltin Chloride → (4-Morpholin-4-yl-phenyl)-(5-tributylstannanyl-[1,2,4]triazolo[1,5-a]pyrazin-8-yl)-carbamic acid tert-butyl ester

HRID 605918
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HRID 605918 반응식
[C:1]([O:5][C:6](=[O:30])[N:7]([C:20]1[C:21]2[N:22]([N:27]=[CH:28][N:29]=2)[C:23](Br)=[CH:24][N:25]=1)[C:8]1[CH:13]=[CH:12][C:11]([N:14]2[CH2:19][CH2:18][O:17][CH2:16][CH2:15]2)=[CH:10][CH:9]=1)([CH3:4])([CH3:3])[CH3:2].C([Mg]Cl)(C)C.[CH2:36]([Sn:40](Cl)([CH2:45][CH2:46][CH2:47][CH3:48])[CH2:41][CH2:42][CH2:43][CH3:44])[CH2:37][CH2:38][CH3:39]>C1COCC1>[C:1]([O:5][C:6](=[O:30])[N:7]([C:8]1[CH:13]=[CH:12][C:11]([N:14]2[CH2:19][CH2:18][O:17][CH2:16][CH2:15]2)=[CH:10][CH:9]=1)[C:20]1[C:21]2[N:22]([N:27]=[CH:28][N:29]=2)[C:23]([Sn:40]([CH2:41][CH2:42][CH2:43][CH3:44])([CH2:45][CH2:46][CH2:47][CH3:48])[CH2:36][CH2:37][CH2:38][CH3:39])=[CH:24][N:25]=1)([CH3:4])([CH3:3])[CH3:2]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 15096Tributyltin ChlorideHCID 86619661(5-Bromo-[1,2,4]triazolo[1,5-a]pyrazin-8-yl)-(4-morpholin-4-yl-phenyl)-carbamic acid tert-butyl esterHCID 178418918HCID 178418918, 화합물

생성물 1

HCID 67047357(4-Morpholin-4-yl-phenyl)-(5-tributylstannanyl-[1,2,4]triazolo[1,5-a]pyrazin-8-yl)-carbamic acid tert-butyl ester

시약·촉매·용매 1

HCID 8028
Tetrahydrofuran
용매
2회

실험 절차

To a cooled (−78° C.) solution of (5-bromo-[1,2,4]triazolo[1,5-a]pyrazin-8-yl)-(4-morpholin-4-yl-phenyl)-carbamic acid tert-butyl ester (370 mg, 0.78 mmol) in THF (12 mL), are added 2M isopropylmagnesium chloride in THF (0.78 mL, 1.56 mmol), and after 5 minutes stirring, tributyltin chloride (0.42, 1.56 mmol) is added. The reaction mixture is stirred at −78° C. for 15 minutes and at room temperature for an additional 15 minutes. After removing the solvent, the residue is purified by silica gel column chromatography eluting with 5:1 petroleum ether:ethyl acetate followed by 1:1 petroleum ether:ethyl acetate. The title compound is isolated (105 mg, 20%).

후처리

  1. stirringThe reaction mixture is stirred at −78° C. for 15 minutes and at room temperature for an additional 15 minutes
  2. customAfter removing the solvent
  3. customthe residue is purified by silica gel column chromatography
  4. washeluting with 5:1 petroleum ether

출처 및 근거

ORD 기록
ord-0cf44ccba9cb4b35a009337ef0ac7cb0
출처 데이터셋
uspto-grants-2011_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07915256B2

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