N-methoxy-N-methyl-3-(6-(4-phenoxyphenylamino)pyrimidin-4-ylamino)benzamide → 1-(3-(6-(4-Phenoxyphenylamino)pyrimidin-4-ylamino)phenyl)but-2-yn-1-one

HRID 404811Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 404811
CON(C)[C:4](=[O:32])[C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([NH:11][C:12]2[CH:17]=[C:16]([NH:18][C:19]3[CH:24]=[CH:23][C:22]([O:25][C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=4)=[CH:21][CH:20]=3)[N:15]=[CH:14][N:13]=2)[CH:6]=1.[C:34]([Mg]Br)#[C:35][CH2:36]C>C1COCC1>[O:25]([C:22]1[CH:23]=[CH:24][C:19]([NH:18][C:16]2[N:15]=[CH:14][N:13]=[C:12]([NH:11][C:7]3[CH:6]=[C:5]([C:4](=[O:32])[C:34]#[C:35][CH3:36])[CH:10]=[CH:9][CH:8]=3)[CH:17]=2)=[CH:20][CH:21]=1)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Komponenten

4

Edukt 2

HCID 57708272N-methoxy-N-methyl-3-(6-(4-phenoxyphenylamino)pyrimidin-4-ylamino)benzamideHCID 178448415HCID 178448415, Verbindung

Produkt 1

HCID 426017411-(3-(6-(4-Phenoxyphenylamino)pyrimidin-4-ylamino)phenyl)but-2-yn-1-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

To a stirred solution of N-methoxy-N-methyl-3-(6-(4-phenoxyphenylamino)pyrimidin-4-ylamino)benzamide (50 mg, 0.11 mmol) in THF (0.5 mL) at 0° C. was added a THF solution of 1-butynylmagnesium bromide (1.1 mL, 1.1 mmol). The reaction mixture was allowed to come to rt and was stirred at rt for 30 min. The reaction mixture was quenched with saturated NH4Cl solution (0.5 mL) and was extracted with EtOAc (2×3 mL). The combined EtOAc layer was washed with brine, was dried over anhydrous Na2SO4, was filtered and was concentrated under reduced pressure to give a white solid, which h was further purified by column chromatography (SiO2, 60-120, chloroform/methanol, 9/1) to give 1-(3-(6-(4-phenoxyphenylamino)pyrimidin-4-ylamino)phenyl)but-2-yn-1-one (I-88) as an off-yellow solid. 1H NMR (DMSO-d6) 5 ppm: 2.22 (s, 3H), 6.16 (s, 1H), 6.97 (d, J=8.6 Hz, 2H), 7.01 (d, J=8.8 Hz, 2H), 7.1 (t, J=7.2 Hz, 1H), 7.35-7.39 (m, 2H), 7.48 (t, J=8 Hz, 1H), 7.56 (d, J=8.8 Hz, 2H), 7.66 (d, J=7.2 Hz, 1H), 7.95 (d, J=7.6 Hz, 1H), 8.32 (s, 1H), 8.39 (s, 1H), 9.22 (s, 1H), 9.47 (s, 1H); LCMS: m/e 421.1 (M+1).

Aufarbeitung

  1. customto come to rt
  2. customThe reaction mixture was quenched with saturated NH4Cl solution (0.5 mL)
  3. extractionwas extracted with EtOAc (2×3 mL)
  4. washThe combined EtOAc layer was washed with brine
  5. dry with materialwas dried over anhydrous Na2SO4
  6. filtrationwas filtered
  7. concentrationwas concentrated under reduced pressure
  8. customto give a white solid, which h
  9. customwas further purified by column chromatography (SiO2, 60-120, chloroform/methanol, 9/1)

Quellen und Nachweise

ORD-Eintrag
ord-59abff2912c9404db74c0aad4a24ff93
Quelldatensatz
uspto-grants-2014_06
Patentnummer
US08748606B2

Notizen zur Reaktion

Wird geladen…