Water → 1-[(1,3-Benzothiazol-2-yl)methyl]-3-methyl-7-(2-butyn-1-yl)-8-bromo-xanthine

HRID 1773324Notes

Reaction equation

HRID 1773324 reaction equation
[CH3:1][N:2]1[C:10]2[N:9]=[C:8]([Br:11])[N:7]([CH2:12][C:13]#[C:14][CH3:15])[C:6]=2[C:5](=[O:16])[NH:4][C:3]1=[O:17].C(=O)([O-])[O-].[K+].[K+].Br[CH2:25][C:26]1[S:27][C:28]2[CH:34]=[CH:33][CH:32]=[CH:31][C:29]=2[N:30]=1.O>CN(C)C=O>[S:27]1[C:28]2[CH:34]=[CH:33][CH:32]=[CH:31][C:29]=2[N:30]=[C:26]1[CH2:25][N:4]1[C:5](=[O:16])[C:6]2[N:7]([CH2:12][C:13]#[C:14][CH3:15])[C:8]([Br:11])=[N:9][C:10]=2[N:2]([CH3:1])[C:3]1=[O:17]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 27762582-(Bromomethyl)-1,3-benzothiazoleHCID 210889278-Bromo-7-(2-butyn-1-yl)-3,7-dihydro-3-methyl-1H-purine-2,6-dione

Product 1

HCID 1180349991-[(1,3-Benzothiazol-2-yl)methyl]-3-methyl-7-(2-butyn-1-yl)-8-bromo-xanthineYield 90%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

By utilizing the well known method, 3-methyl-7-(2-butyn-1-yl)-8-bromo-xanthine 1a (327 mg, 1 mmol) was dissolved in N,N-dimethylformamide (5 ml). Potassium carbonate (221 mg, 1.6 mmol) and 2-bromomethyl-1,3-benzothiazole (228 mg, 1 mmol) were added to give a reaction mixture. The reaction mixture was reacted overnight at room temperature and TLC was used to monitor the reaction progress. After the reaction was completed, the obtained reaction mixture was poured into water, suction filtered, and the obtained solid was washed with water, dried to give 1-[(1,3-benzothiazol-2-yl)methyl]-3-methyl-7-(2-butyn-1-yl)-8-bromo-xanthine 2b (400 mg, yellow solid), yield: 90%.

Workup

  1. customto give a reaction mixture
  2. customThe reaction mixture was reacted overnight at room temperature
  3. customthe obtained reaction mixture
  4. filtrationfiltered
  5. washthe obtained solid was washed with water
  6. customdried

Sources & evidence

ORD record
ord-a344a0b6e1254354a8c6aa1abc01f6b4
Source dataset
uspto-grants-2016_02
Patent number
US09255098B2

Reaction notes

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