Sodium Hydroxide → N2,N4-bis(4-carboxy-3-methoxyphenyl)-5-fluoro-2,4-pyrimidinediamine

HRID 76654

Reaktionsgleichung

Reaktionsgleichung von HRID 76654
C(C1C=C(NC2N=C(NC3C=CC=C(C(O)=O)C=3)C(F)=CN=2)C=CC=1)(O)=O.[CH3:28][O:29][C:30]1[CH:31]=[C:32]([NH:40][C:41]2[N:46]=[C:45]([NH:47][C:48]3[CH:53]=[CH:52][C:51]([C:54]([O:56]C)=[O:55])=[C:50]([O:58][CH3:59])[CH:49]=3)[C:44]([F:60])=[CH:43][N:42]=2)[CH:33]=[CH:34][C:35]=1[C:36]([O:38]C)=[O:37].[OH-].[Na+]>>[C:36]([C:35]1[CH:34]=[CH:33][C:32]([NH:40][C:41]2[N:46]=[C:45]([NH:47][C:48]3[CH:53]=[CH:52][C:51]([C:54]([OH:56])=[O:55])=[C:50]([O:58][CH3:59])[CH:49]=3)[C:44]([F:60])=[CH:43][N:42]=2)=[CH:31][C:30]=1[O:29][CH3:28])([OH:38])=[O:37]

Komponenten

4

Edukt 3

HCID 14798Sodium HydroxideHCID 10126258N2,N4-bis(3-carboxyphenyl)-5-fluoro-2,4-pyrimidinediamineHCID 22060643N2,N4-bis(3-methoxy-4-methoxycarbonylphenyl)-5-fluoro-2,4-pyrimidinediamine

Produkt 1

HCID 22060868N2,N4-bis(4-carboxy-3-methoxyphenyl)-5-fluoro-2,4-pyrimidinediamineAusbeute 70 %

Versuchsvorschrift

In a manner analogous to the preparation of N2,N4-bis(3-carboxyphenyl)-5-fluoro-2,4-pyrimidinediamine, N2,N4-bis(3-methoxy-4-methoxycarbonylphenyl)-5-fluoro-2,4-pyrimidinediamine (30 mg, 0.06 mmol) and NaOH (200 mg, 5 mmol) gave N2,N4-bis(4-carboxy-3-methoxyphenyl)-5-fluoro-2,4-pyrimidinediamine (18 mg, 64%) as a white solid. 1H NMR (DMSO-d6): δ 3.66 (s, 3H), 3.73 (s, 3H), 7.37 (d, J=8.4 Hz, 1H), 7.47 (s, 1H), 7.49 (s, 1H), 7.61-7.71 (m, 3H), 8.25 (d, J=3.6 Hz, 1H), 9.65 (s, 1H, NH), 9.70 (s, 1H, NH); 19F NMR (282 MHz, DMSO-d6): δ−162.11; LCMS: ret. time: 17.25 min.; purity: 100%; MS (m/e): 429.04 (MH+).

Quellen und Nachweise

ORD-Eintrag
ord-de6655d8c051419f9cc76a079734217a
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08835430B2

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