Sodium Hydroxide → HCID 67388966, compound

HRID 905657Notes

Reaction equation

HRID 905657 reaction equation
C([O:3][C:4]([C:6]1[C:7]([NH:13][C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([CH:20]([OH:22])[CH3:21])[CH:15]=2)=[N:8][C:9](Cl)=[N:10][CH:11]=1)=[O:5])C.Cl.[Cl:24][C:25]1[CH:26]=[C:27]([CH2:33][CH2:34][NH2:35])[CH:28]=[C:29]([Cl:32])[C:30]=1[OH:31].C(N(C(C)C)CC)(C)C.[OH-].[Na+]>CN1C(=O)CCC1.CO.C1COCC1>[Cl:24][C:25]1[CH:26]=[C:27]([CH2:33][CH2:34][NH:35][C:9]2[N:8]=[C:7]([NH:13][C:14]3[CH:19]=[CH:18][CH:17]=[C:16]([CH:20]([OH:22])[CH3:21])[CH:15]=3)[C:6]([C:4]([OH:3])=[O:5])=[CH:11][N:10]=2)[CH:28]=[C:29]([Cl:32])[C:30]=1[OH:31]

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 81531DiisopropylethylamineHCID 23071601HCID 23071601, compoundHCID 86602002HCID 86602002, compound

Product 1

HCID 67388966HCID 67388966, compound

Reagents, catalysts & solvents 2

HCID 13387N-methyl-2-pyrrolidoneSolventHCID 21899815MeOH tetrahydrofuranSolvent

Procedure

2-Chloro-4-{[3-(1-hydroxyethyl)phenyl]amino}pyrimidine-5-carboxylic acid ethyl ester synthesized in accordance with the method described in WO 99/31073 and 2-(3,5-dichloro-4-hydroxyphenyl)ethylamine hydrochloride were allowed to undergo the reaction at 80 to 90° C. in NMP in the presence of diisopropylethylamine, and the resulting compound was allowed to react with 1 M sodium hydroxide aqueous solution under heating in a mixed methanol-THF solution to obtain 2-{[2-(3,5-dichloro-4-hydroxyphenyl)ethyl]amino}-4-{[3-(1-hydroxyethyl)phenyl]amino}pyrimidine-5-carboxylic acid. F: 463

Sources & evidence

ORD record
ord-5b23c4c4f3614104875b833beaa5439c
Source dataset
uspto-grants-2011_09
Patent number
US08012959B2

Reaction notes

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