Hexane ethanol triethylamine → (+)-1-{4-[4-(2-tert-Butyl-6-propylpyrimidin-4-yl)piperazin-1-yl]pentyl}-5-methyl-1H-pyrimidine-2,4-dione

HRID 1678090Notes

Reaction equation

HRID 1678090 reaction equation
[Cl-].[C:2]([C:6]1[N:11]=[C:10]([N:12]2[CH2:17][CH2:16][NH+:15]([CH:18]([CH3:31])[CH2:19][CH2:20][CH2:21][N:22]3[CH:27]=[C:26]([CH3:28])[C:25](=[O:29])[NH:24][C:23]3=[O:30])[CH2:14][CH2:13]2)[CH:9]=[C:8]([CH2:32][CH2:33][CH3:34])[N:7]=1)([CH3:5])([CH3:4])[CH3:3].CCCCCC.C(O)C.C(N(CC)CC)C>CCCCCC.C(O)(C)C>[C:2]([C:6]1[N:11]=[C:10]([N:12]2[CH2:13][CH2:14][N:15]([CH:18]([CH3:31])[CH2:19][CH2:20][CH2:21][N:22]3[CH:27]=[C:26]([CH3:28])[C:25](=[O:29])[NH:24][C:23]3=[O:30])[CH2:16][CH2:17]2)[CH:9]=[C:8]([CH2:32][CH2:33][CH3:34])[N:7]=1)([CH3:4])([CH3:5])[CH3:3]

Participants

4

Reactant 2

HCID 19048314Hexane ethanol triethylamineHCID 673739654-(2-tert-butyl-6-propylpyrimidin-4-yl)-1-[1-methyl-4-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1 (2H)-yl)butyl]piperazin-1-ium chloride

Product 1

HCID 10389364(+)-1-{4-[4-(2-tert-Butyl-6-propylpyrimidin-4-yl)piperazin-1-yl]pentyl}-5-methyl-1H-pyrimidine-2,4-dioneYield 43.2%

Reagents, catalysts & solvents 1

HCID 21585144Isopropanol hexaneSolvent

Procedure

For racemate resolution, a solution of 4-(2-tert-butyl-6-propylpyrimidin-4-yl)-1-[1-methyl-4-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1 (2H)-yl)butyl]piperazin-1-ium chloride from Example 38 (200 mg) in 3 ml of hexane/isopropanol (9:1 (V/V)) was loaded onto a chiral column (DAICEL ChiralPAK AD, length: 50 cm, internal diameter: 5 cm, particle size: 20μ); eluent: hexane/ethanol/triethylamine (85:15:0.1 (V/V)). 0.08 g of the title compound was obtained after concentration of the resulting filtrate.

Sources & evidence

ORD record
ord-5ca8618c6cd64d92b83afb4e7fa807fb
Source dataset
uspto-grants-2011_08
Patent number
US08008488B2

Reaction notes

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