Potassium Carbonate → 1,3-Dimethyl-7-[4-[4-(2-morpholinoethoxy)benzoyl]-benzyl]xanthine

HRID 1291418Notes

Reaction equation

HRID 1291418 reaction equation
[OH:1][C:2]1[CH:29]=[CH:28][C:5]([C:6]([C:8]2[CH:27]=[CH:26][C:11]([CH2:12][N:13]3[C:21]4[C:20](=[O:22])[N:19]([CH3:23])[C:18](=[O:24])[N:17]([CH3:25])[C:16]=4[N:15]=[CH:14]3)=[CH:10][CH:9]=2)=[O:7])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Cl.Cl[CH2:38][CH2:39][N:40]1[CH2:45][CH2:44][O:43][CH2:42][CH2:41]1>CN(C=O)C.O>[CH3:23][N:19]1[C:20](=[O:22])[C:21]2[N:13]([CH2:12][C:11]3[CH:26]=[CH:27][C:8]([C:6](=[O:7])[C:5]4[CH:28]=[CH:29][C:2]([O:1][CH2:38][CH2:39][N:40]5[CH2:45][CH2:44][O:43][CH2:42][CH2:41]5)=[CH:3][CH:4]=4)=[CH:9][CH:10]=3)[CH:14]=[N:15][C:16]=2[N:17]([CH3:25])[C:18]1=[O:24]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 77210Morpholine, 4-(2-chloroethyl)-, hydrochloride (1:1)HCID 189190737-[4-(4-Hydroxybenzoyl)benzyl)-1,3-dimethylxanthine

Product 1

HCID 189193401,3-Dimethyl-7-[4-[4-(2-morpholinoethoxy)benzoyl]-benzyl]xanthineYield 42.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of 7-[4-(4-hydroxybenzoyl)benzyl)-1,3-dimethylxanthine (170 mg), potassium carbonate (200 mg) and 1-chloro-2-morpholinoethane hydrochloride (87 mg) in DMF (10 ml) was stirred at 60° C. for 5 hours. This reaction mixture was poured in water and extracted with ethyl acetate. The extract was washed with water, dried, and concentrated. The residue was purified by silica gel column chromatography (chloroform: ethyl acetate: acetone =1:1:1) to provide the title compound (93 mg).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with water
  3. customdried
  4. concentrationconcentrated
  5. customThe residue was purified by silica gel column chromatography (chloroform: ethyl acetate: acetone =1:1:1)

Sources & evidence

ORD record
ord-3c81753bec9f4322a5ce73533cd02e5b
Source dataset
uspto-grants-1998_05
Patent number
US05753664

Reaction notes

Loading…