Chloroform → 1-(6-Dimethylamino-3-hydroxy-3-methyl-4-hexynyl)-3-methyl-7-propylxanthine

HRID 1738791Notes

Reaction equation

HRID 1738791 reaction equation
[CH3:1][N:2]([CH2:4][C:5]#[CH:6])[CH3:3].C([Li])CCC.[CH3:12][N:13]1[C:21]2[N:20]=[CH:19][N:18]([CH2:22][CH2:23][CH3:24])[C:17]=2[C:16](=[O:25])[N:15]([CH2:26][CH2:27][C:28](=[O:30])[CH3:29])[C:14]1=[O:31].C(Cl)(Cl)Cl>CCCCCC.O1CCCC1>[CH3:1][N:2]([CH3:3])[CH2:4][C:5]#[C:6][C:28]([OH:30])([CH3:29])[CH2:27][CH2:26][N:15]1[C:16](=[O:25])[C:17]2[N:18]([CH2:22][CH2:23][CH3:24])[CH:19]=[N:20][C:21]=2[N:13]([CH3:12])[C:14]1=[O:31]

Participants

7

Reactant 4

HCID 6212ChloroformHCID 81643N,N-DimethylpropargylamineHCID 153909233-Methyl-1-(3-oxobutyl)-7-propylxanthineHCID 178418339Butyllithium

Product 1

HCID 153909071-(6-Dimethylamino-3-hydroxy-3-methyl-4-hexynyl)-3-methyl-7-propylxanthine

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Procedure

4.32 g (52 mmol) of N,N-dimethyl-2-propynylamine, 32.4 ml (52 mmol) of n-butyllithium as 1.6 M solution in n-hexane and 11.1 g (40 mmol) of 3-methyl-1-(3-oxobutyl)-7-propylxanthine were reacted in tetrahydrofuran and worked up in analogy to Example 1C2), but using chloroform in place of dichloromethane as extractant.

Sources & evidence

ORD record
ord-3ce9ef70eda24bb09c26eb6b840e994a
Source dataset
uspto-grants-1999_10
Patent number
US05965555

Reaction notes

Loading…