Diisopropylamine → HCID 18460833, compound

HRID 905658Notes

Reaction equation

HRID 905658 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:7](Cl)=[N:8][C:9]([Cl:12])=[N:10][CH:11]=1)=[O:5])[CH3:2].[NH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([CH3:21])[CH:16]=1.C(NC(C)C)(C)C>C(#N)C>[CH2:1]([O:3][C:4]([C:6]1[C:7]([NH:14][C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([CH3:21])[CH:16]=2)=[N:8][C:9]([Cl:12])=[N:10][CH:11]=1)=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 7912DiisopropylamineHCID 7934m-ToluidineHCID 104020Ethyl 2,4-dichloropyrimidine-5-carboxylate

Product 1

HCID 18460833HCID 18460833, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

2,4-Dichloropyrimidine-5-carboxylic ethyl ester and m-toluidine were allowed to undergo the reaction in acetonitrile in the presence of diisopropylamine to obtain 2-chloro-4-[(3-methylphenyl)amino]pyrimidine-5-carboxylic ethyl ester. Said ester compound was hydrolyzed in THF with 1 M sodium hydroxide aqueous solution, and the resulting carboxylic acid compound was allowed to react with oxalyl chloride in dichloromethane in the presence of a catalytic amount of DMF and then treated with a mixture of aqueous ammonia and ice to obtain 2-chloro-4-[(3-methylphenyl)amino]pyrimidine-5-carboxamide. F: 263.

Sources & evidence

ORD record
ord-fdcae36291cb4af6a1c39dab5738471f
Source dataset
uspto-grants-2011_09
Patent number
US08012959B2

Reaction notes

Loading…