Diisopropylethylamine → 8-Bromo-7-(2-butyn-1-yl)-3,7-dihydro-3-methyl-1H-purine-2,6-dione

HRID 1986522Notes

Reaction equation

HRID 1986522 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].C(N(C(C)C)CC)(C)C.Br[CH2:24][C:25]#[C:26][CH3:27]>CN(C)C=O.O>[CH3:1][N:2]1[C:10]2[N:9]=[C:8]([Br:11])[N:7]([CH2:24][C:25]#[C:26][CH3:27])[C:6]=2[C:5](=[O:12])[NH:4][C:3]1=[O:13]

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 15487978-bromo-3-methyl-3,7-dihydro-1H-purine-2,6-dioneHCID 27568621-Bromo-2-butyne2×

Product 1

HCID 210889278-Bromo-7-(2-butyn-1-yl)-3,7-dihydro-3-methyl-1H-purine-2,6-dione

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 40.00 g of 3-methyl-8-bromoxanthine, 36 ml of diisopropylethylamine and 23.00 g of 1-bromo-2-butyne in 500 ml of N,N-dimethylformamide is stirred at room temperature for three hours. 1 ml of 1-bromo-2-butyne is then added again and the mixture is stirred at room temperature for a further hour until the reaction is complete. For work-up, the reaction mixture is diluted with 400 ml of water. The resulting precipitate is filtered off with suction, washed with water, cold methanol and diethyl ether and dried.

Workup

  1. stirringthe mixture is stirred at room temperature for a further hour until the reaction
  2. filtrationThe resulting precipitate is filtered off with suction
  3. washwashed with water, cold methanol and diethyl ether
  4. customdried

Sources & evidence

ORD record
ord-493ec07cc32545e3a8ca71cfb5793bf8
Source dataset
uspto-grants-2009_06
Patent number
US07550455B2

Reaction notes

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