4-(3-(4-fluorophenyl)-1H-pyrazol-4-yl]-N-[(4-methoxyphenyl)methyl]-2-pyrimidinamine → 4-[3-(4-fluorophenyl)-1H-pyrazol-4-yl]-2-pyrimidinamine

HRID 1060933Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1060933
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:12]([C:13]3[CH:18]=[CH:17][N:16]=[C:15]([NH:19]CC4C=CC(OC)=CC=4)[N:14]=3)=[CH:11][NH:10][N:9]=2)=[CH:4][CH:3]=1>FC(F)(F)C(O)=O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:12]([C:13]3[CH:18]=[CH:17][N:16]=[C:15]([NH2:19])[N:14]=3)=[CH:11][NH:10][N:9]=2)=[CH:4][CH:3]=1

Komponenten

3

Edukt 1

HCID 1784909824-(3-(4-fluorophenyl)-1H-pyrazol-4-yl]-N-[(4-methoxyphenyl)methyl]-2-pyrimidinamine

Produkt 1

HCID 1785083854-[3-(4-fluorophenyl)-1H-pyrazol-4-yl]-2-pyrimidinamine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6422Trifluoroacetic acidLösungsmittel

Versuchsvorschrift

A solution of 4-[3-(4-fluorophenyl)-1H-pyrazol-4-yl]-N-[(4-methoxyphenyl)methyl]-2-pyrimidinamine prepared in accordance with Example A-305 (0.35 g, 0.00093 mol) in 15 mL of trifluoroacetic acid was heated at reflux for 16 hours. Solvent was removed and the residue was partitioned between ethyl acetate and 1 N ammonia hydroxide. Organic layer was washed with brine, dried over magnesium sulfate and filtered. The filtrate was concentrated and purified by chromatography on silica gel (ethyl acetate) to give 0.14 g of product, 4-[3-(4-fluorophenyl)-1H-pyrazol-4-yl]-2-pyrimidinamine, as a pale yellow solid (59% yield), mp: 273-274° C.; Anal. Calc'd for C13H10FN5 0.25 H2O: C, 60.11; H, 4.07; N, 26.96. Found: C, 60.15; H, 3.82; N, 26.38.

Aufarbeitung

  1. temperatureat reflux for 16 hours
  2. customSolvent was removed
  3. customthe residue was partitioned between ethyl acetate and 1 N ammonia hydroxide
  4. washOrganic layer was washed with brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated
  8. custompurified by chromatography on silica gel (ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-273bf030f95243c596a776892a2a5cea
Quelldatensatz
uspto-grants-2003_02
Patentnummer
US06525059B1

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