Xanthine → HCID 13747693, compound

HRID 1762549Notes

Reaction equation

[OH-].[K+].[CH3:3][N:4]1[C:12]2[N:11]=[CH:10][N:9]([CH2:13][CH2:14][CH3:15])[C:8]=2[C:7](=[O:16])[NH:6][C:5]1=[O:17].[K].N1C(=O)C2NC=NC=2NC1=O.Cl[CH2:31][CH2:32][CH2:33][C:34]([OH:37])([CH3:36])[CH3:35]>CO.CN(C)C=O>[OH:37][C:34]([CH3:36])([CH3:35])[CH2:33][CH2:32][CH2:31][N:6]1[C:7](=[O:16])[C:8]2[N:9]([CH2:13][CH2:14][CH3:15])[CH:10]=[N:11][C:12]=2[N:4]([CH3:3])[C:5]1=[O:17]

Participants

Conditions

Temperature: 80 °C

Procedure

A solution of 5.6 g (0.1 mol) of potassium hydroxide in 100 ml of methanol is added to a suspension of 20.8 g (0.1 mol) of 3-methyl-7-propylxanthine in 250 ml of methanol. On heating, a clear solution forms, and this is evaporated to dryness under reduced pressure. The potassium salt of the xanthine compound which remains is intensively dried under a high vacuum, 500 ml of dimethylformamide and 15.0 g (0.11 mol) of the tertiary alcohol from stage (a) are added and the mixture is stirred at 80° C. for 18 hours. The mixture is worked up analogously to Example 5b, whereupon 25.1 g of crude product (81.4% of theory) are obtained and can be purified by recrystallization from diisopropyl ether, with the addition of a little ethyl acetate, at the boiling point.

Workup

temperatureOn heating
customa clear solution forms, and this is evaporated to dryness under reduced pressure
additionare added
customare obtained
customcan be purified by recrystallization from diisopropyl ether, with the addition of a little ethyl acetate, at the boiling point

Sources & evidence

ORD record: ord-ed6f1a9bfef74ccaa75f4f79a9ba3e94
Source dataset: uspto-grants-1989_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04833146

Reaction notes

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