Dimethylformamide → 8-Bromo-7-(2-butyn-1-yl)-3,7-dihydro-3-methyl-1H-purine-2,6-dione
Reaction equation
[CH3:1][N:2]1[C:10]2[N:9]=[C:8]([Br:11])[NH:7][C:6]=2[C:5](=[O:12])[NH:4][C:3]1=[O:13].CN(C)C=O.C(N(C(C)C)CC)(C)C.Br[CH2:29][C:30]#[C:31][CH3:32]>O>[CH3:1][N:2]1[C:10]2[N:9]=[C:8]([Br:11])[N:7]([CH2:29][C:30]#[C:31][CH3:32])[C:6]=2[C:5](=[O:12])[NH:4][C:3]1=[O:13]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 85 °C
Procedure
3-Methyl-8-bromo-xanthine (30 gm) and N,N-dimethylformamide (170 mL) were charged into a 1000 mL round bottomed flask equipped with a mechanical stirrer. Diisopropylethylamine (DIPEA, 15.9 gm) and 1-bromo-2-butyne (16.2 gm) were added at 30° C. The reaction mixture was heated to 85° C. and maintained the temperature for 4 hours. The reaction mixture was cooled to 30° C. and pre cooled water (300 mL) was added. The solid formed was collected by filtration and washed with pre cooled water (150 mL) and diethyl ether (30 mL). The solid was dried in oven under vacuum at 50° C. to get 30.9 gm of the title compound.
Workup
- customequipped with a mechanical stirrer
- temperaturemaintained the temperature for 4 hours
- temperatureThe reaction mixture was cooled to 30° C.
- additionwas added
- customThe solid formed
- filtrationwas collected by filtration
- washwashed with pre
- temperaturecooled water (150 mL) and diethyl ether (30 mL)
- customThe solid was dried in oven under vacuum at 50° C.
Sources & evidence
- ORD record
- ord-42ad3127e7f24e73b51993b6188c5b2b
- Source dataset
- uspto-grants-2015_06
- Patent number
- US09056112B2
Reaction notes
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