Water → 1-[(5-Fluoro-1,3-benzothiazol-2-yl)methyl]-3-methyl-7-(2-butyn-1-yl)-8-bromo-xanthine

HRID 1773322Notes

Reaction equation

HRID 1773322 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].Br[CH2:19][C:20]1[S:21][C:22]2[CH:28]=[CH:27][C:26]([F:29])=[CH:25][C:23]=2[N:24]=1.C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[F:29][C:26]1[CH:27]=[CH:28][C:22]2[S:21][C:20]([CH2:19][N:4]3[C:5](=[O:16])[C:6]4[N:7]([CH2:12][C:13]#[C:14][CH3:15])[C:8]([Br:11])=[N:9][C:10]=4[N:2]([CH3:1])[C:3]3=[O:17])=[N:24][C:23]=2[CH:25]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 144586272-(Bromomethyl)-5-fluorobenzo[d]thiazoleHCID 210889278-Bromo-7-(2-butyn-1-yl)-3,7-dihydro-3-methyl-1H-purine-2,6-dione

Product 1

HCID 1180352331-[(5-Fluoro-1,3-benzothiazol-2-yl)methyl]-3-methyl-7-(2-butyn-1-yl)-8-bromo-xanthineYield 99%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

By utilizing the well known method, 3-methyl-7-(2-butyn-1-yl)-8-bromo-xanthine 1a (156 mg, 0.53 mmol) was dissolved in N,N-dimethylformamide (3 ml). 2-bromomethyl-5-fluoro-1,3-benzothiazole (140 mg, 0.57 mmol), potassium carbonate (118 mg, 0.79 mmol) were added to give a reaction mixture. The obtained 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-[(5-fluoro-1,3-benzothiazol-2-yl)methyl]-3-methyl-7-(2-butyn-1-yl)-8-bromo-xanthine 1b (240 mg, off-white solid), yield: 99%.

Workup

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

Sources & evidence

ORD record
ord-cccf6aabf6ca414c9fcba29d32fea29a
Source dataset
uspto-grants-2016_02
Patent number
US09255098B2

Reaction notes

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