3-Aminobenzonitrile → 2-chloro-N4-(3-cyanophenyl)-5-fluoro-4-pyrimidineamine

HRID 76574

Reaktionsgleichung

Reaktionsgleichung von HRID 76574
C1COC2C=CC(NC3C(F)=CN=C(NC4C=CC=C(O)C=4)N=3)=CC=2O1.[NH2:27][C:28]1[CH:29]=[C:30]([CH:33]=[CH:34][CH:35]=1)[C:31]#[N:32].[Cl:36][C:37]1[N:42]=[C:41](Cl)[C:40]([F:44])=[CH:39][N:38]=1>>[Cl:36][C:37]1[N:42]=[C:41]([NH:27][C:28]2[CH:35]=[CH:34][CH:33]=[C:30]([C:31]#[N:32])[CH:29]=2)[C:40]([F:44])=[CH:39][N:38]=1

Komponenten

4

Edukt 3

HCID 167023-AminobenzonitrileHCID 2507052,4-Dichloro-5-fluoropyrimidineHCID 22060334N4-(3,4-ethylenedioxyphenyl)-5-fluoro-N2-(3-hydroxyphenyl)-2,4-primidinediamine

Produkt 1

HCID 220604572-chloro-N4-(3-cyanophenyl)-5-fluoro-4-pyrimidineamineAusbeute 86 %

Versuchsvorschrift

In a manner analogous to the preparation of N4-(3,4-ethylenedioxyphenyl)-5-fluoro-N2-(3-hydroxyphenyl)-2,4-pyrimidinediamine, 3-aminobenzonitrile (142 mg, 1.2 mmol) and 2,4-dichloro-5-fluoropyrimidine (100 mg, 0.6 mmol) gave 2-chloro-N4-(3-cyanophenyl)-5-fluoro-4-pyrimidineamine (128 mg, 86%) as a white solid. The reaction of 2-chloro-N4-(3-cyanophenyl)-5-fluoro-4-pyrimidineamine (50 mg, 0.2 mmol) and 3-aminophenol (66 mg, 0.6 mmol) gave N4-(3-cyanophenyl)-5-fluoro-N2-(3-hydroxyphenyl)-2,4-pyrimidinediamine (40 mg, 62%). 1H NMR (acetone-d6): δ 6.48 (ddd, J=0.9, 2.4 and 7.8 Hz, 1H), 7.10 (t, J=8.1 Hz, 1H), 7.18 (ddd, J=1.2, 2.1 and 8.1 Hz, 1H), 7.33 (t, J=2.1 Hz, 1H), 7.45 (dt, J=1.2 and 7.8 Hz, 1H), 7.54 (t, J=8.1 Hz, 1H), 8.08 (d, J=3.3 Hz, 1H), 8.14 (ddd, J=1.5, 2.7 and 8.4 Hz, 1H), 8.39 (t, J=2.1 Hz, 1H), 8.58 (s, 1H, NH), 8.84 (s, 1H, NH); 19F NMR (282 MHz, acetone-d6): δ−167.41; LCMS: ret. time: 17.75 min.; purity: 92.39%; MS (m/e): 322.59 (MH+).

Quellen und Nachweise

ORD-Eintrag
ord-0a1fe060221340af819af91c1aa016f6
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08835430B2

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