Reaktionsgleichung
Cl[C:2]1[N:7]=[C:6]([NH:8][N:9]2[CH:13]=[CH:12][CH:11]=[CH:10]2)[C:5]([F:14])=[CH:4][N:3]=1.[CH:15]([O:18][C:19]1[CH:25]=[CH:24][C:22]([NH2:23])=[CH:21][CH:20]=1)([CH3:17])[CH3:16]>>[F:14][C:5]1[C:6]([NH:8][N:9]2[CH:13]=[CH:12][CH:11]=[CH:10]2)=[N:7][C:2]([NH:23][C:22]2[CH:21]=[CH:20][C:19]([O:18][CH:15]([CH3:17])[CH3:16])=[CH:25][CH:24]=2)=[N:3][CH:4]=1Komponenten
3
Versuchsvorschrift
In like manner to the preparation of N4-(3,4-ethylenedioxyphenyl)-5-fluoro-N2-(3-hydroxyphenyl)-2,4-pyrimidinediamine, 2-chloro-5-fluoro-N-(1H-pyrrol-1-yl)-4-pyrimidineamine was reacted with 4-isopropoxyaniline to produce 5-fluoro-N2-(4-isopropoxyphenyl)-N4-(1H-pyrrol-1-yl)-2,4-pyrimidinediamine. 1H NMR (DMSO-d6): δ 10.69 (s, 1H), 9.03 (s, 1H), 8.06 (d, 1H, J=3.5 Hz), 7.30 (d, 2H, J=9.3 Hz), 6.82 (t, 2H, J=2.3 Hz), 6.58 (d, 2H, J=9.3 Hz), 6.11 (t, 2H, J=2.3 Hz), 4.41 (sept, 1H, J=5.8 Hz), 1.18 (d, 6H, J=5.8 Hz). LCMS: ret. time: 21.21 min.; purity: 90%; MS (m/e): 328 (MH+).
Quellen und Nachweise
- ORD-Eintrag
- ord-94131dccf67e462ab8ca97bbd9319226
- Quelldatensatz
- uspto-grants-2014_09
- Patentnummer
- US08835430B2
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