2-Bromopropane → 7-Benzyl-3-isopropylxanthine

HRID 323867Notes

Reaction equation

[CH2:1]([N:8]1[C:16]2[C:15](=[O:17])[NH:14][C:13](=[O:18])[NH:12][C:11]=2[N:10]=[CH:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].Br[CH:22]([CH3:24])[CH3:23]>CN(C)C=O.O.CO>[CH2:1]([N:8]1[C:16]2[C:15](=[O:17])[NH:14][C:13](=[O:18])[N:12]([CH:22]([CH3:24])[CH3:23])[C:11]=2[N:10]=[CH:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 50 °C

Procedure

A solution of 3.5 g (1.45 mmol) of 7-benzylxanthine from Example 6b) in 60 ml of dimethylformamide was heated to 50° C. and treated in portions with 0.35 g (1.45 mmol) of sodium hydride, diluted with 20 ml of dimethylformamide and stirred at 50° C. for one hour. 1.36 ml (1.45 mmol) of 2-bromopropane were added to this suspension and the temperature was increased to 80° C. In the course of the reaction, a total of 4.91 ml (52.3 mmol) of 2-bromopropane were additionally added. After a total of 16 hours at 80° C., 10 ml of water and 2 ml of methanol were added, and the mixture was stirred for 10 minutes, treated with a further 70 ml of water and extracted three times using 70 ml of methyl tert-butyl ether each time. The organic phases were washed with water, dried using magnesium sulfate and concentrated under reduced pressure. The crude product was purified by flash chromatography on a silica gel column, dichloromethane/methanol (19/0.4).

Workup

temperaturethe temperature was increased to 80° C
customIn the course of the reaction
stirringthe mixture was stirred for 10 minutes
extractionextracted three times
washThe organic phases were washed with water
customdried
concentrationconcentrated under reduced pressure
customThe crude product was purified by flash chromatography on a silica gel column, dichloromethane/methanol (19/0.4)

Sources & evidence

ORD record: ord-2a0d56e9c43f4d07a72ddda07541b69f
Source dataset: uspto-grants-2001_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06214992B1

Reaction notes

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