Bromine → 3-Bromo-7-(1,1-dimethoxyethyl)imidazo[1,2-a]pyrimidine

HRID 1796092Notes

Reaction equation

HRID 1796092 reaction equation
[CH3:1][O:2][C:3]([C:7]1[CH:12]=[CH:11][N:10]2[CH:13]=[CH:14][N:15]=[C:9]2[N:8]=1)([O:5][CH3:6])[CH3:4].[Br-:16].[K+].C([O-])(=O)C.[Na+].BrBr.S([O-])([O-])=O.[Na+].[Na+]>CO>[Br:16][C:13]1[N:10]2[CH:11]=[CH:12][C:7]([C:3]([O:5][CH3:6])([O:2][CH3:1])[CH3:4])=[N:8][C:9]2=[N:15][CH:14]=1

Participants

7

Reactant 5

HCID 24408BromineHCID 24437Sodium SulfiteHCID 253877Potassium BromideHCID 517045Sodium AcetateHCID 180012777-(1,1-Dimethoxyethyl)imidazo[1,2-a]pyrimidine

Product 1

HCID 180012923-Bromo-7-(1,1-dimethoxyethyl)imidazo[1,2-a]pyrimidineYield 69%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of 7-(1,1-dimethoxyethyl)imidazo[1,2-α]pyrimidine (5.3 g, 26 mmol), potassium bromide (3.1 g, 26 mmol) and sodium acetate (3.2 g, 39 mmol) in methanol (50 ml) was cooled to 0° C. before dropwise addition of bromine (4.5 g, 28 mmol) over 10 min. After stirring at 0° C. for a further 15 min the reaction was treated with 1M sodium sulphite solution (5 ml) and the solvent removed in vacuo. The residue was treated with dichloromethane (100 ml) then saturated sodium hydrogencarbonate solution (100 ml) was added. After stirring vigorously for 10 min the organic layer was collected, washed with 1M sodium sulphite solution (100 ml), water, brine, dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. Trituration of the residue with diethyl ether furnished 3-bromo-7-(1,1-dimethoxyethyl)imidazo[1,2-α]pyrimidine (5.05 g, 69%) as a cream-coloured solid: δH (360 MHz, CDCl3) 1.70 (3H, s), 3.28 (6H, s), 7.43 (1H, d, J 7), 7.82 (1H, s), 8.39 (1H, d, J 7).

Workup

  1. customthe solvent removed in vacuo
  2. additionThe residue was treated with dichloromethane (100 ml)
  3. additionsaturated sodium hydrogencarbonate solution (100 ml) was added
  4. stirringAfter stirring vigorously for 10 min the organic layer
  5. customwas collected
  6. washwashed with 1M sodium sulphite solution (100 ml), water, brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-641531276cbd4fd4a5a7763cda674667
Source dataset
uspto-grants-2006_04
Patent number
US07030128B2

Reaction notes

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