Sodium Carbonate → 3-cyclopropyl-N-((2,4-dimethoxy-6-vinylpyrimidin-5-yl)methyl)-1-ethyl-1H-pyrazol-5-amine

HRID 80859

Reaktionsgleichung

Reaktionsgleichung von HRID 80859
Cl[C:2]1[C:7]([CH2:8][NH:9][C:10]2[N:14]([CH2:15][CH3:16])[N:13]=[C:12]([CH:17]3[CH2:19][CH2:18]3)[CH:11]=2)=[C:6]([O:20][CH3:21])[N:5]=[C:4]([O:22][CH3:23])[N:3]=1.[CH3:24][C:25]1(C)C(C)(C)OB(C=C)O1.C(=O)([O-])[O-].[Na+].[Na+]>COCCOC.O.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>[CH:17]1([C:12]2[CH:11]=[C:10]([NH:9][CH2:8][C:7]3[C:6]([O:20][CH3:21])=[N:5][C:4]([O:22][CH3:23])=[N:3][C:2]=3[CH:24]=[CH2:25])[N:14]([CH2:15][CH3:16])[N:13]=2)[CH2:19][CH2:18]1

Komponenten

7

Edukt 3

HCID 10340Sodium CarbonateHCID 52330122-Ethenyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolaneHCID 86690292N-((4-chloro-2,6-dimethoxypyrimidin-5-yl)methyl)-3-cyclopropyl-1-ethyl-1H-pyrazol-5-amine

Produkt 1

HCID 866902933-cyclopropyl-N-((2,4-dimethoxy-6-vinylpyrimidin-5-yl)methyl)-1-ethyl-1H-pyrazol-5-amine

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 962WaterLösungsmittelHCID 80711,2-DimethoxyethaneLösungsmittel

Versuchsvorschrift

To a solution of N-((4-chloro-2,6-dimethoxypyrimidin-5-yl)methyl)-3-cyclopropyl-1-ethyl-1H-pyrazol-5-amine (2.42 g, 7.16 mmol) in DME (50 mL) and water (15 mL) was added 4,4,5,5-tetramethyl-2-vinyl-1,3,2-dioxaborolane (2.5 mL, 14.3 mmol), Pd(Ph3P)4 (0.828 g, 0.716 mmol) and sodium carbonate (2.47 g, 23.3 mmol). The mixture was sparged with argon for 15 min and then heated at reflux for 18 h. The mixture was then absorbed onto silica gel and dried under reduced pressure. After dry loading, the product was purified by FCC (10-75% EtOAc/heptane) to give 3-cyclopropyl-N-((2,4-dimethoxy-6-vinylpyrimidin-5-yl)methyl)-1-ethyl-1H-pyrazol-5-amine. MS (ESI+) m/z 330.1 (M+H)+.

Aufarbeitung

  1. customThe mixture was sparged with argon for 15 min
  2. temperatureheated
  3. temperatureat reflux for 18 h
  4. customThe mixture was then absorbed onto silica gel
  5. customdried under reduced pressure
  6. customAfter dry loading
  7. customthe product was purified by FCC (10-75% EtOAc/heptane)

Quellen und Nachweise

ORD-Eintrag
ord-0c2d60243c7b4d8db4b4634857a6857c
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08846656B2

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