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

HRID 405539

Reaction equation

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:35]=[CH:34][C:33]([NH:36][C:37]2[N:42]=[C:41]([NH:43][C:44]3[CH:49]=[CH:48][C:47]([O:50][CH3:51])=[C:46]([C:52]([O:54]C)=[O:53])[CH:45]=3)[C:40]([F:56])=[CH:39][N:38]=2)=[CH:32][C:31]=1[C:57]([O:59]C)=[O:58].[OH-].[Na+]>>[C:57]([C:31]1[CH:32]=[C:33]([NH:36][C:37]2[N:42]=[C:41]([NH:43][C:44]3[CH:49]=[CH:48][C:47]([O:50][CH3:51])=[C:46]([C:52]([OH:54])=[O:53])[CH:45]=3)[C:40]([F:56])=[CH:39][N:38]=2)[CH:34]=[CH:35][C:30]=1[O:29][CH3:28])([OH:59])=[O:58]

Participants

Reactant 3

HCID 14798Sodium Hydroxide

HCID 10126258N2,N4-bis(3-carboxyphenyl)-5-fluoro-2,4-pyrimidinediamine

HCID 22060426HCID 22060426, compound

Product 1

HCID 22060733N2,N4-bis(3-carboxy-4-methoxyphenyl)-5-fluoro-2,4-pyrimidinediamineYield 103.8%

Procedure

In a manner analogous to the preparation of N2,N4-bis(3-carboxyphenyl)-5-fluoro-2,4-pyrimidinediamine, N2,N4-bis[4-methoxy-3-(methoxycarbonyl)phenyl]-5-fluoro-2,4-pyrimidinediamine (80 mg, 0.18 mmol) and NaOH (200 mg, 5 mmol) gave N2,N4-bis(3-carboxy-4-methoxyphenyl)-5-fluoro-2,4-pyrimidinediamine (80 mg). 1H NMR (DMSO-d6): δ 3.75 (s, 3H), 3.80 (s, 3H), 6.94 (d, J=9.6 Hz, 1H), 7.05 (d, J=9.3 Hz, 1H), 7.78-7.80 (m, 3H), 7.94 (dd, J=9.3 Hz, 1H), 8.04 (d, J=3.6 Hz, 1H), 9.10 (s, 1H, NH), 9.30 (s, 1H, NH); 19F NMR (282 MHz, DMSO-d6): δ −165.56; LCMS: ret. time: 14.65 min.; purity: 100%; MS (m/e): 428.83 (MH+).

Sources & evidence

ORD record: ord-55cffd03449442cb80662980b321f176
Source dataset: uspto-grants-2014_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08748597B2

Linked notes

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