1,2-Dichloroethane → 2-[N,N-bis(tert-butoxycarbonyl)amino]-5-(ter-butyl-dimethyl-silanyloxymethyl)-pyrimidin

HRID 1789865노트

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HRID 1789865 반응식
[C:1]([O:5][C:6]([N:8]([C:16]1[N:21]=[CH:20][C:19](Br)=[CH:18][N:17]=1)[C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:23]([Si:27](C)(C)OC[Sn](CCCC)(CCCC)CCCC)([CH3:26])([CH3:25])[CH3:24].C([O:47][CH2:48][CH3:49])C.[F-].[K+].Cl[CH2:53]CCl>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>[C:1]([O:5][C:6]([N:8]([C:16]1[N:21]=[CH:20][C:19]([C:48]([CH3:49])([CH3:53])[O:47][SiH2:27][C:23]([CH3:26])([CH3:25])[CH3:24])=[CH:18][N:17]=1)[C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])=[O:7])([CH3:4])([CH3:3])[CH3:2]

참가 물질

7

반응물 5

HCID 111,2-DichloroethaneHCID 3283Diethyl EtherHCID 522689Potassium FluorideHCID 11977091tert-butyl N-(5-bromopyrimidin-2-yl)-N-((tert-butoxy)carbonyl)carbamateHCID 14270862Tert-butyl-dimethyl-(tributylstannylmethoxy)silane

생성물 1

HCID 1317258312-[N,N-bis(tert-butoxycarbonyl)amino]-5-(ter-butyl-dimethyl-silanyloxymethyl)-pyrimidin수율 55%

시약·촉매·용매 1

HCID 178418476HCID 178418476, 화합물촉매2회

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온도
0 °C

실험 절차

A solution of 2-[N,N-bis(tert-butoxycarbonyl)amino]-5-bromopyrimidin (16.0 g, 45.0 mmol), tert-butyl-dimethyl-tributylstannanylmethoxy-silane (20.5 g, 47.1 mmol), and bis(triphenylphosphine)palladium(II) dichloride (1.00 g, 1.40 mmol) in 1,2-dichloroethane (50 mL) was stirred at reflux overnight. Additional bis(triphenylphosphine)palladium(II) dichloride (1.00 g, 1.40 mmol) was added and the solution was refluxed for 8 h. The mixture was cooled to 0° C. and diethyl ether (200 mL) was added followed by saturated aqueous potassium fluoride (50 mL). The mixture was stirred vigourously for 60 min and filtered. The organic phase was washed with water, dried and concentrated under reduced pressure. Flash chromatography (MeOH/CH2Cl2, 1:99) gave 2-[N,N-bis(tert-butoxycarbonyl)amino]-5-(tert-butyl-dimethyl-silanyloxymethyl)-pyrimidin (10.2 g, 55%).

후처리

  1. temperatureat reflux overnight
  2. temperaturethe solution was refluxed for 8 h
  3. filtrationfiltered
  4. washThe organic phase was washed with water
  5. customdried
  6. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-867b195600854178ac824c7615cb1d97
출처 데이터셋
uspto-grants-2006_07
특허 번호
US07071175B1

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