Lithium Hydroxide → N2-(2-carboxyindol-5-yl)-5-fluoro-N4-(3-hydroxyphenyl)-2,4-pyrimidinediamine

HRID 76670Notes

Reaction equation

HRID 76670 reaction equation
C(C1C=CC(NC2C(F)=CN=C(NC3C=CC4OC(C(O)=O)CC=4C=3)N=2)=CC=1)(C)(C)C.C([O:34][C:35]([C:37]1[NH:38][C:39]2[C:44]([CH:45]=1)=[CH:43][C:42]([NH:46][C:47]1[N:52]=[C:51]([NH:53][C:54]3[CH:59]=[CH:58][CH:57]=[C:56]([OH:60])[CH:55]=3)[C:50]([F:61])=[CH:49][N:48]=1)=[CH:41][CH:40]=2)=[O:36])C.[Li+].[OH-]>>[C:35]([C:37]1[NH:38][C:39]2[C:44]([CH:45]=1)=[CH:43][C:42]([NH:46][C:47]1[N:52]=[C:51]([NH:53][C:54]3[CH:59]=[CH:58][CH:57]=[C:56]([OH:60])[CH:55]=3)[C:50]([F:61])=[CH:49][N:48]=1)=[CH:41][CH:40]=2)([OH:36])=[O:34]

Participants

4

Reactant 3

HCID 3939Lithium HydroxideHCID 22060366N4-(4-tert-butylphenyl)-5-fluoro-N2-(2,3-dihydro-2-carboxybenzofuran-5-yl)-2,4-pyrimidinediamineHCID 22060970N2-(2-ethoxycarbonylindol-5-yl)-5-fluoro-N4-(3-hydroxyphenyl)-2,4-pyrimidinediamine

Product 1

HCID 22060545N2-(2-carboxyindol-5-yl)-5-fluoro-N4-(3-hydroxyphenyl)-2,4-pyrimidinediamine

Procedure

In a manner similar to the preparation of N4-(4-tert-butylphenyl)-5-fluoro-N2-[2,3-dihydro-2-(carboxy)benzofuran-5-yl]-2,4-pyrimidinediamine, N2-(2-ethoxycarbonylindol-5-yl)-5-fluoro-N4-(3-hydroxyphenyl)-2,4-pyrimidinediamine upon LiOH treatment gave N2-(2-carboxyindol-5-yl)-5-fluoro-N4-(3-hydroxyphenyl)-2,4-pyrimidinediamine. 1H NMR (CD3OD): δ 7.83 (m, 1H), 7.73 (s, 1H), 7.50 (bd, 1H, J=8.7 Hz), 7.30-7.11 (m, 5H), 6.68 (bd, 1H); LCMS: ret. time: 16.50 min.; purity: 97%; MS (m/e): 380 (MH+).

Sources & evidence

ORD record
ord-8b132978f03546a3a20ea0fb25c66068
Source dataset
uspto-grants-2014_09
Patent number
US08835430B2

Reaction notes

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