6-Chlorohexan-2-one → 7-Benzyl-3-methyl-1-(5-oxohexyl)xanthine

HRID 1762541Notes

Reaction equation

HRID 1762541 reaction equation
[CH2:1]([N:8]1[C:16]2[C:15](=[O:17])[NH:14][C:13](=[O:18])[N:12]([CH3:19])[C:11]=2[N:10]=[CH:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl[CH2:21][CH2:22][CH2:23][CH2:24][C:25](=[O:27])[CH3:26]>>[CH2:1]([N:8]1[C:16]2[C:15](=[O:17])[N:14]([CH2:21][CH2:22][CH2:23][CH2:24][C:25](=[O:27])[CH3:26])[C:13](=[O:18])[N:12]([CH3:19])[C:11]=2[N:10]=[CH:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 824686-Chlorohexan-2-oneHCID 6856307-Benzyl-3-methylxanthine

Product 1

HCID 200411277-Benzyl-3-methyl-1-(5-oxohexyl)xanthineYield 90.4%

Procedure

The compound was also accessible, inter alia, by first reacting 7-benzyl-3-methylxanthine with 1-chloro-5-hexanone under the reaction conditions described above to give 7-benzyl-3-methyl-1-(5-oxohexyl)-xanthine (yield 90.4% of theory, melting point: 82°-84° C.) and then reductively methylating the oxohexyl side chain with methylmagnesium chloride in anhydrous ether analogously to Example 9 (yield: 60.2% of theory; melting point: 108°-110° C.).

Workup

  1. customunder the reaction conditions

Sources & evidence

ORD record
ord-f6ab901c84be423b84344d8dcc200b81
Source dataset
uspto-grants-1989_05
Patent number
US04833146

Reaction notes

Loading…