Benzyl Bromide → HCID 54017981, compound

HRID 1417161Notes

Reaction equation

HRID 1417161 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][CH3:10])[N:6]=[C:5]([C:11]2([OH:27])[C:15]3=[N:16][CH:17]=[CH:18][C:19]([C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=4)=[C:14]3[C:13](=[O:26])[O:12]2)[N:4]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:34](Br)[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1>CN(C)C=O>[CH3:10][O:9][C:7]1[CH:8]=[C:3]([O:2][CH3:1])[N:4]=[C:5]([C:11]([C:15]2[N:16]=[CH:17][CH:18]=[C:19]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[C:14]=2[C:13]([O:26][CH2:34][C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)=[O:12])=[O:27])[N:6]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 70346079HCID 70346079, compound

Product 1

HCID 54017981HCID 54017981, compoundYield 81.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

0.5 g of 7-(4,6-dimethoxypyrimidin-2-yl)-7-hydroxy-4-phenylfuro[3,4-b]pyridin-5(7H)one was dissolved in 10 ml of N,N-dimethylformamide, and 0.2 g of potassium carbonate was added thereto. Then, the reaction solution was stirred sufficiently. 0.23 g of benzyl bromide was added dropwise to the reaction solution at room temperature, and the reaction solution was stirred for one day. The reaction solution was poured into ice water and extracted with ethyl acetate. The extract was sufficiently washed with water and then dried over anhydrous magnesium sulfate. The solvent was distilled off, and the resulting crude crystals were washed with isopropyl ether to obtain 0.5 g (yield 80%) of the desired compound. m.p.: 124°-126° C.

Workup

  1. stirringthe reaction solution was stirred for one day
  2. extractionextracted with ethyl acetate
  3. washThe extract was sufficiently washed with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationThe solvent was distilled off
  6. washthe resulting crude crystals were washed with isopropyl ether

Sources & evidence

ORD record
ord-106d72904719482e8bcd4bfa4387ba21
Source dataset
uspto-grants-1999_03
Patent number
US05877120

Reaction notes

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