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Potassium Phosphate, Tribasic → N,N-Di(Boc)-3-ethynyl-5-[4-(isopropylsulfonyl)phenyl]pyrazin-2-amine

HRID 78659
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 78659
Br[C:2]1[N:3]=[C:4]([C:23]#[C:24][Si](C)(C)C)[C:5]([N:8]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[N:6][CH:7]=1.[CH:29]([S:32]([C:35]1[CH:40]=[CH:39][C:38](B(O)O)=[CH:37][CH:36]=1)(=[O:34])=[O:33])([CH3:31])[CH3:30].[O-]P([O-])([O-])=O.[K+].[K+].[K+].S(S([O-])=O)([O-])(=O)=O.[Na+].[Na+]>CC#N.CC(C)([P](C(C)(C)C)([Pd][P](C(C)(C)C)(C(C)(C)C)C(C)(C)C)C(C)(C)C)C.O.C(OCC)(=O)C>[C:23]([C:4]1[C:5]([N:8]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[N:6][CH:7]=[C:2]([C:38]2[CH:37]=[CH:36][C:35]([S:32]([CH:29]([CH3:31])[CH3:30])(=[O:34])=[O:33])=[CH:40][CH:39]=2)[N:3]=1)#[CH:24]
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Komponenten

9

Edukt 4

HCID 62657Potassium Phosphate, TribasicHCID 656671Sodium PyrosulfiteHCID 441193274-(Isopropylsulphonyl)benzeneboronic acidHCID 58070279Tert-butyl N-tert-butoxycarbonyl-N-[5-bromo-3-((trimethylsilyl)ethynyl)pyrazin-2-yl]carbamate

Produkt 1

HCID 59471983N,N-Di(Boc)-3-ethynyl-5-[4-(isopropylsulfonyl)phenyl]pyrazin-2-amine

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 178418851HCID 178418851, VerbindungKatalysatorHCID 962WaterLösungsmittel2×HCID 6342AcetonitrileLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

tert-butyl N-[5-bromo-3-(2-trimethylsilylethynyl)pyrazin-2-yl]-N-tert-butoxycarbonyl-carbamate (3 g, 6.377 mmol) and (4-isopropylsulfonylphenyl)boronic acid (1.491 g, 6.536 mmol) were dissolved in MeCN (60.00 mL) then treated with water (12.00 mL) and K3PO4 (2.706 g, 12.75 mmol) then degassed/flushed nitrogen (×5 cycles). Treated with Pd[P(tBu)3]2 (162.9 mg, 0.3188 mmol) and reflushed Vac/Nitrogen ×5. The resulting mixture was stirred at room temperature for 1 h. The reaction mixture was poured quickly into a mixture of ethyl acetate (500 mL), water (90 mL) and 1% aqueous sodium metabisulphite at 4° C., shaken well and the layer separated. The organic fraction was dried over MgSO4, filtered and the filtrate was treated with 3-mercaptopropyl ethyl sulphide on silica (0.8 mmol/g)(1 g), pre-absorbed onto silica gel then purified by column chromatography on silica gel eluting with 30-40% EtOAc/petroleu ether. Product fractions were combined and concentrated in vacuo to leave the product as a yellow/ brown viscous oil. Triturated with petroleum ether and some diethyl ether and a small amount of dichloromethane added. Left to stand at room temperature for 30 min and beige crystals formed, isolated by filtration to leave the product as a beige solid (1.95 g, 61%); 1H NMR (400 MHz, DMSO) d 1.20 (m, 6H), 1.39 (s, 18H), 3.50 (m, 1H), 5.01 (s, 1H), 8.03 (m, 2H), 8.46 (m, 2H) and 9.37 (s, 1H) ppm.

Aufarbeitung

  1. stirringshaken well
  2. customthe layer separated
  3. dry with materialThe organic fraction was dried over MgSO4
  4. filtrationfiltered
  5. additionthe filtrate was treated with 3-mercaptopropyl ethyl sulphide on silica (0.8 mmol/g)(1 g)
  6. custompre-absorbed onto silica gel
  7. customthen purified by column chromatography on silica gel eluting with 30-40% EtOAc/petroleu ether
  8. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-28689bb3683e4eb9a18ca90aa27776b8
Quelldatensatz
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08841308B2

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