1-Methylpiperazine → 2-Tert-butyl-4-(4-methylpiperazin-1-yl)pyrimidine-5-carboxylic acid

HRID 1930380Notes

Reaction equation

HRID 1930380 reaction equation
[C:1]([C:5]1[N:10]=[C:9](Cl)[C:8]([C:12]([O:14]CC)=[O:13])=[CH:7][N:6]=1)([CH3:4])([CH3:3])[CH3:2].[CH3:17][N:18]1[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]1>CN1C(=O)CCC1>[C:1]([C:5]1[N:10]=[C:9]([N:21]2[CH2:22][CH2:23][N:18]([CH3:17])[CH2:19][CH2:20]2)[C:8]([C:12]([OH:14])=[O:13])=[CH:7][N:6]=1)([CH3:2])([CH3:3])[CH3:4]

Participants

4

Reactant 2

HCID 531671-MethylpiperazineHCID 24903912Ethyl 2-(tert-butyl)-4-chloropyrimidine-5-carboxylate

Product 1

HCID 692975142-Tert-butyl-4-(4-methylpiperazin-1-yl)pyrimidine-5-carboxylic acidYield 32%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

Using a procedure analogous to Example B40, ethyl 2-tert-butyl-4-chloropyrimidine-5-carboxylate from Example B40 (0.30 g, 1.24 mmol) and 1-methylpiperazine (0.62 g, 6.18 mmol) in presence of NMP (catalytic amount) were combined to afford 2-tert-butyl-4-(4-methylpiperazin-1-yl)pyrimidine-5-carboxylic acid (0.11 g, 32% yield). MS (ESI) m/z: 279.0 (M+H+).

Sources & evidence

ORD record
ord-24cd7feb2990438a8b2166aecfb95349
Source dataset
uspto-grants-2012_05
Patent number
US08188113B2

Reaction notes

Loading…