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

HRID 76669Notes

Reaction equation

HRID 76669 reaction equation
C([C:5]1[CH:10]=[CH:9][C:8]([NH:11][C:12]2[C:17]([F:18])=[CH:16][N:15]=[C:14]([NH:19][C:20]3[CH:21]=[CH:22][C:23]4[O:27][CH:26]([C:28]([OH:30])=[O:29])[CH2:25][C:24]=4[CH:31]=3)[N:13]=2)=[CH:7][CH:6]=1)(C)(C)C.[Li+].[OH-:33]>>[C:28]([C:26]1[O:27][C:23]2[CH:22]=[CH:21][C:20]([NH:19][C:14]3[N:13]=[C:12]([NH:11][C:8]4[CH:9]=[CH:10][CH:5]=[C:6]([OH:33])[CH:7]=4)[C:17]([F:18])=[CH:16][N:15]=3)=[CH:31][C:24]=2[CH:25]=1)([OH:30])=[O:29]

Participants

3

Reactant 2

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

Product 1

HCID 22060888N2-(2-carboxybenzofuran-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, 5-fluoro-N4-(3-hydroxyphenyl)-N2-(2-methoxycarbonylbenzofuran-5-yl)-4-pyrimidinediamine upon LiOH treatment gave N2-(2-carboxybenzofuran-5-yl)-5-fluoro-N4-(3-hydroxyphenyl)-2,4-pyrimidinediamine. 1H NMR (CD3OD): δ 7.97 (bd, 2H), 7.60-7.44 (m, 4H), 7.20-7.05 (m, 3H), 6.69 (bd, 1H); 19F NMR (CD3OD): −21844; LCMS: ret. time: 16.77 min.; purity: 100%; MS (m/e): 381 (MH+).

Sources & evidence

ORD record
ord-fabae6a1b9634f06984f5bc20c6834d7
Source dataset
uspto-grants-2014_09
Patent number
US08835430B2

Reaction notes

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