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Cesium fluoride → 5-chloro-N-(6-methoxypyridin-3-yl)-3-(2-methyl-6-(methylthio)pyrimidin-4-yl)pyrazin-2-amine

HRID 1812240
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1812240
Br[C:2]1[C:3]([NH:9][C:10]2[CH:11]=[N:12][C:13]([O:16][CH3:17])=[CH:14][CH:15]=2)=[N:4][CH:5]=[C:6]([Cl:8])[N:7]=1.[F-].[Cs+].[CH3:20][C:21]1[N:26]=[C:25]([S:27][CH3:28])[CH:24]=[C:23]([Sn](CCCC)(CCCC)CCCC)[N:22]=1>O1CCOCC1.O.[Cu]I.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Cl:8][C:6]1[N:7]=[C:2]([C:23]2[CH:24]=[C:25]([S:27][CH3:28])[N:26]=[C:21]([CH3:20])[N:22]=2)[C:3]([NH:9][C:10]2[CH:11]=[N:12][C:13]([O:16][CH3:17])=[CH:14][CH:15]=2)=[N:4][CH:5]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

8

Edukt 3

HCID 25953Cesium fluorideHCID 595482802-Methyl-4-(methylthio)-6-(tributylstannyl)pyrimidineHCID 866470673-bromo-5-chloro-N-(6-methoxypyridin-3-yl)pyrazin-2-amine

Produkt 1

HCID 866470685-chloro-N-(6-methoxypyridin-3-yl)-3-(2-methyl-6-(methylthio)pyrimidin-4-yl)pyrazin-2-amineAusbeute 73 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 24350
Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)
Katalysator
HCID 178418397HCID 178418397, VerbindungKatalysator
HCID 962WaterLösungsmittel
HCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
140 °C

Versuchsvorschrift

A glass microwave reaction vessel was charged with 3-bromo-5-chloro-N-(6-methoxypyridin-3-yl)pyrazin-2-amine (83 mg, 0.263 mmol), copper (I) iodide (10 mg, 0.053 mmol, Aldrich), cesium fluoride (80 mg, 0.526 mmol, Alfa Aesar), tetrakis(triphenylphosphine)palladium(0) (30.4 mg, 0.026 mmol) and 2-methyl-4-(methylthio)-6-(tributylstannyl)pyrimidine (113 mg, 0.263 mmol) in dioxane (2 mL). The reaction mixture was stirred and heated in a Emrys Optimizer microwave reactor (Personal Chemistry, Biotage AB, Inc., Upssala, Sweden) at 140° C. for 30 min. The reaction mixture was diluted with water (10 mL) and extracted with CH2Cl2 (2×30 mL). The combined organic extracts were washed with saturated NaCl (10 mL) and dried over Na2SO4. The solution was filtered and concentrated in vacuo to give the crude material as a yellow solid. The crude product was purified by silica gel chromatography eluting with 10% EtOAc/hexanes to give 5-chloro-N-(6-methoxypyridin-3-yl)-3-(2-methyl-6-(methylthio)pyrimidin-4-yl)pyrazin-2-amine (72 mg, 0.192 mmol, 73.0% yield). 1H NMR (300 MHz, CDCl3) δ 2.63 (s, 3H) 2.78 (s, 3H) 3.95 (s, 3H) 6.79 (d, J=8.77 Hz, 1H) 8.01 (dd, J=8.70, 2.12 Hz, 1H) 8.17 (d, J=5.55 Hz, 2H) 8.39 (s, 1H) 12.21 (s, 1H). m/z (ESI, +ve ion) 375.0 (M+H)+.

Aufarbeitung

  1. customA glass microwave reaction vessel
  2. extractionextracted with CH2Cl2 (2×30 mL)
  3. washThe combined organic extracts were washed with saturated NaCl (10 mL)
  4. dry with materialdried over Na2SO4
  5. filtrationThe solution was filtered
  6. concentrationconcentrated in vacuo
  7. customto give the crude material as a yellow solid
  8. customThe crude product was purified by silica gel chromatography
  9. washeluting with 10% EtOAc/hexanes

Quellen und Nachweise

ORD-Eintrag
ord-8b65b03a0cbd4acf9f66def1e06db29b
Quelldatensatz
uspto-grants-2013_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08362241B2

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