Diisobutylaluminumhydride → (1-(2-chloro-5-fluoropyrimidin-4-yl)-3-methyl-1H-pyrazol-4-yl)methanol

HRID 469173Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 469173
[Cl:1][C:2]1[N:7]=[C:6]([N:8]2[CH:12]=[C:11]([C:13](OCC)=[O:14])[C:10]([CH3:18])=[N:9]2)[C:5]([F:19])=[CH:4][N:3]=1.[H-].C([Al+]CC(C)C)C(C)C>O1CCCC1.C1(C)C=CC=CC=1>[Cl:1][C:2]1[N:7]=[C:6]([N:8]2[CH:12]=[C:11]([CH2:13][OH:14])[C:10]([CH3:18])=[N:9]2)[C:5]([F:19])=[CH:4][N:3]=1

Komponenten

5

Edukt 2

HCID 21225700DiisobutylaluminumhydrideHCID 86659253ethyl 1-(2-chloro-5-fluoropyrimidin-4-yl)-3-methyl-1H-pyrazole-4-carboxylate

Produkt 1

HCID 58513701(1-(2-chloro-5-fluoropyrimidin-4-yl)-3-methyl-1H-pyrazol-4-yl)methanolAusbeute 90 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1140TolueneLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of ethyl 1-(2-chloro-5-fluoropyrimidin-4-yl)-3-methyl-1H-pyrazole-4-carboxylate 1 (4.9 g, 17.2 mmol) in 60 mL of anhydrous tetrahydrofuran (THF), was slowly added 38 mL (38 mmol) of 1M solution of di-isobutylaluminum hydride (DIBAL) in toluene with ice bath cooling. After being stirred for 2 hours at the same temperature, the reaction was quenched by slow addition of 1N-NaOH solution. It was diluted with ethyl acetate and washed with brine. The collected organic layer was dried over anhydrous sodium sulfate and then partially concentrated in vacou. To this, n-hexanes were added to form pale yellow precipitates. The resulting solids were collected by filtration and rinsed with n-hexanes and then dried with high vacuum to give 3.7 g (90%) of Intermediate No. 2; 1H NMR (300 MHz, CDCl3) δ 8.57 (1H, d, J=3.3 Hz), 8.52 (1H, s), 7.94 (1H, s), 4.72 (2H, s); MS (ESI) m/z 243 [M+H]+.

Aufarbeitung

  1. temperaturecooling
  2. customthe reaction was quenched by slow addition of 1N-NaOH solution
  3. additionIt was diluted with ethyl acetate
  4. washwashed with brine
  5. dry with materialThe collected organic layer was dried over anhydrous sodium sulfate
  6. concentrationpartially concentrated in vacou
  7. additionTo this, n-hexanes were added
  8. customto form pale yellow precipitates
  9. filtrationThe resulting solids were collected by filtration
  10. washrinsed with n-hexanes
  11. customdried with high vacuum

Quellen und Nachweise

ORD-Eintrag
ord-8a608183a9304bb998814a65e9bddd04
Quelldatensatz
uspto-grants-2014_01
Patentnummer
US08629132B2

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