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

HRID 734022Notes

Reaction equation

HRID 734022 reaction equation
N1C=CC(N)=NC=1N.[Li+].[OH-].[C:11]([C:15]1[CH:20]=[CH:19][C:18]([NH:21][C:22]2[C:27]([F:28])=[CH:26][N:25]=[C:24]([NH:29][C:30]3[CH:31]=[CH:32][C:33]4[O:37][C:36]([C:38]([O:40]C)=[O:39])=[CH:35][C:34]=4[CH:42]=3)[N:23]=2)=[CH:17][CH:16]=1)([CH3:14])([CH3:13])[CH3:12]>>[C:11]([C:15]1[CH:20]=[CH:19][C:18]([NH:21][C:22]2[C:27]([F:28])=[CH:26][N:25]=[C:24]([NH:29][C:30]3[CH:31]=[CH:32][C:33]4[O:37][C:36]([C:38]([OH:40])=[O:39])=[CH:35][C:34]=4[CH:42]=3)[N:23]=2)=[CH:17][CH:16]=1)([CH3:14])([CH3:12])[CH3:13]

Participants

4

Reactant 3

HCID 3939Lithium HydroxideHCID 674312,4-DiaminopyrimidineHCID 22060304N4-(4-tert-butylphenyl)-5-fluoro-N2-(2-methoxycarbonylbenzofuran-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-641b012d78c84b03be81fd3b6dfa391b
Source dataset
uspto-grants-2009_09
Patent number
US07589200B2

Reaction notes

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