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

HRID 76671Notes

Reaction equation

HRID 76671 reaction equation
[C:1]([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)([CH3:4])([CH3:3])[CH3:2].[Li+].[OH-].C(C1C=CC(NC2C(F)=CN=C(NC3C=CC4OC(C(OC)=O)=CC=4C=3)N=2)=CC=1)(C)(C)C>>[C:1]([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][C:26]([C:28]([OH:30])=[O:29])=[CH:25][C:24]=4[CH:31]=3)[N:13]=2)=[CH:7][CH:6]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 3

HCID 3939Lithium HydroxideHCID 22060304N4-(4-tert-butylphenyl)-5-fluoro-N2-(2-methoxycarbonylbenzofuran-5-yl)-2,4-pyrimidinediamineHCID 22060366N4-(4-tert-butylphenyl)-5-fluoro-N2-(2,3-dihydro-2-carboxybenzofuran-5-yl)-2,4-pyrimidinediamine

Product 1

HCID 22060444N4-(4-tert-butylphenyl)-N2-(2-carboxybenzofuran-5-yl)-5-fluoro-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, LiOH treatment with N4-(4-tert-butylphenyl)-5-fluoro-N2-(2-methoxycarbonylbenzofuran-5-yl)-2,4-pyrimidinediamine gave N4-(4-tert-butylphenyl)-N2-(2-carboxybenzofuran-5-yl)-5-fluoro-2,4-pyrimidinediamine. 1H NMR (CD3OD): δ 9.3 (bd, 2H), 8.25 (s, 1H), 8.10 (s, 1H), 7.65-7.30 (m, 5H), 1.25 (s, 9H); 19F NMR (CD3OD): −21844; LCMS: ret. time: 23.32 min.; purity: 100%; MS (m/e): 421 (MH+).

Sources & evidence

ORD record
ord-4decbf7d8d654a849de2cea563df109f
Source dataset
uspto-grants-2014_09
Patent number
US08835430B2

Reaction notes

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