Water → (E)-8-(4-(4-bromobutoxy)styryl)-1,3-diethyl-7-methylxanthine

HRID 1077535Notes

Reaction equation

HRID 1077535 reaction equation
[CH2:1]([N:3]1[C:12](=[O:13])[C:11]2[N:10]([CH3:14])[C:9](/[CH:15]=[CH:16]/[C:17]3[CH:22]=[CH:21][C:20]([OH:23])=[CH:19][CH:18]=3)=[N:8][C:7]=2[N:6]([CH2:24][CH3:25])[C:4]1=[O:5])[CH3:2].C(=O)([O-])[O-].[K+].[K+].[Br:32][CH2:33][CH2:34][CH2:35][CH2:36]Br.O>CN(C)C=O>[Br:32][CH2:33][CH2:34][CH2:35][CH2:36][O:23][C:20]1[CH:19]=[CH:18][C:17](/[CH:16]=[CH:15]/[C:9]2[N:10]([CH3:14])[C:11]3[C:12](=[O:13])[N:3]([CH2:1][CH3:2])[C:4](=[O:5])[N:6]([CH2:24][CH3:25])[C:7]=3[N:8]=2)=[CH:22][CH:21]=1

Participants

6

Reactant 4

HCID 962WaterHCID 80561,4-DibromobutaneHCID 11430Potassium Carbonate2×HCID 1356653431H-Purine-2,6-dione, 3,7-dihydro-1,3-diethyl-8-(2-(4-hydroxyphenyl)eth enyl)-7-methyl-, (E)-

Product 1

HCID 6448951(E)-8-(4-(4-bromobutoxy)styryl)-1,3-diethyl-7-methylxanthineYield 61%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

Compound 184 (200 mg, 0.59 mmol) obtained in Reference Example 181 was dissolved in 4 ml of dimethylformamide. To the solution were added 163 mg (1.18 mmol) of potassium carbonate and 0.56 ml (1.18 mmol) of 1,4-dibromobutane, and the mixture was stirred at 50° C. for 4 hours. Water was added thereto under ice cooling to dissolve potassium carbonate and the deposited crystals were collected by filtration. The obtained crude crystals were recrystallized from hexane/ethyl acetate to give 170 mg (yield 61%) of Compound 186 as pale yellow grains.

Workup

  1. filtrationthe deposited crystals were collected by filtration
  2. customThe obtained crude crystals
  3. customwere recrystallized from hexane/ethyl acetate

Sources & evidence

ORD record
ord-b32a33aa86374d798a09248b0643c89d
Source dataset
uspto-grants-1996_08
Patent number
US05543415

Reaction notes

Loading…