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

HRID 76648

반응식

HRID 76648 반응식
C(C1C=C(NC2N=C(NC3C=CC=C(C(O)=O)C=3)C(F)=CN=2)C=CC=1)(O)=O.[OH:28][C:29]1[CH:30]=[C:31]([NH:39][C:40]2[N:45]=[C:44]([NH:46][C:47]3[CH:52]=[CH:51][C:50]([C:53]([O:55]C)=[O:54])=[C:49]([OH:57])[CH:48]=3)[C:43]([F:58])=[CH:42][N:41]=2)[CH:32]=[CH:33][C:34]=1[C:35]([O:37]C)=[O:36].[OH-].[Na+]>>[OH:28][C:29]1[CH:30]=[C:31]([NH:39][C:40]2[N:45]=[C:44]([NH:46][C:47]3[CH:52]=[CH:51][C:50]([C:53]([OH:55])=[O:54])=[C:49]([OH:57])[CH:48]=3)[C:43]([F:58])=[CH:42][N:41]=2)[CH:32]=[CH:33][C:34]=1[C:35]([OH:37])=[O:36]

참가 물질

4

반응물 3

HCID 14798Sodium HydroxideHCID 10126258N2,N4-bis(3-carboxyphenyl)-5-fluoro-2,4-pyrimidinediamineHCID 22060199N2,N4-bis[3-hydroxy-4-(methoxycarbonyl)phenyl]-5-fluoro-2,4-pyrimidinediamine

생성물 1

HCID 22060865N2,N4-bis(3-hydroxy-4-carboxyphenyl)-5-fluoro-2,4-pyrimidinediamine수율 78.1%

실험 절차

In a manner analogous to the preparation of N2,N4-bis(3-carboxyphenyl)-5-fluoro-2,4-pyrimidinediamine, the reaction of N2,N4-bis[3-hydroxy-4-(methoxycarbonyl)phenyl]-5-fluoro-2,4-pyrimidinediamine (70 mg, 0.16 mmol) and NaOH (100 mg, 2.5 mmol) gave N2,N4-bis(3-hydroxy-4-carboxyphenyl)-5-fluoro-2,4-pyrimidinediamine (50 mg, 77%) as a white solid. 1H NMR (DMSO-d6): δ 7.21 (dd, J=1.5 and 8.7 Hz, 1H), 7.46-7.52 (m, 3H), 7.63 (d, J=8.7 Hz, 1H), 7.72 (d, J=8.7 Hz, 1H), 8.28 (d, J=3.3 Hz, 1H), 9.71 (s, 1H, NH), 9.79 (s, 1H, NH), 11.34 (br, 2H); 19F NMR (282 MHz, DMSO-d6): δ−161.10; LCMS: ret. time: 20.76 min.; purity: 84.65%; MS (m/e): 400.95 (MH+).

출처 및 근거

ORD 기록
ord-49c1a394622e49e8be97692971bc879e
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08835430B2

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