Imidazole → 3-Bromo-7-(tert-butyldimethylsilanyloxymethyl)imidazo[1,2-a]pyrimidine

HRID 478231Notes

Reaction equation

HRID 478231 reaction equation
[Br:1][C:2]1[N:6]2[CH:7]=[CH:8][C:9]([CH2:11][OH:12])=[N:10][C:5]2=[N:4][CH:3]=1.N1C=CN=C1.[Si:18](Cl)([C:21]([CH3:24])([CH3:23])[CH3:22])([CH3:20])[CH3:19]>ClCCl>[Br:1][C:2]1[N:6]2[CH:7]=[CH:8][C:9]([CH2:11][O:12][Si:18]([C:21]([CH3:24])([CH3:23])[CH3:22])([CH3:20])[CH3:19])=[N:10][C:5]2=[N:4][CH:3]=1

Participants

5

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 180012743-Bromoimidazo[1,2-a]pyrimidin-7-ylmethanol

Product 1

HCID 697084433-Bromo-7-(tert-butyldimethylsilanyloxymethyl)imidazo[1,2-a]pyrimidineYield 100.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

3-Bromoimidazo[1,2-a]pyrimidin-7-ylmethanol (912 mg, 4.00 mmol) was dissolved in dichloromethane (10 ml) and treated with imidazole (0.70 g, 10.3 mmol) and tert-butyldimethylsilyl chloride (0.77 g, 5.1 mmol) and the mixture left to stir at ambient temperature for 1 h. The reaction was diluted with dichloromethane (75 ml) and washed with 0.01N hydrochloric acid (2×50 ml). The organic phase was washed with saturated sodium hydrogencarbonate solution (50 ml), water (50 ml) and brine (50 ml), dried over anhydrous magnesium sulfate, filtered and evaporated to give crude 3-bromo-7-(tert-butyldimethylsilanyloxymethyl)imidazo[1,2-a]pyrimidine (1.37 g, 100%) as a yellow solid.

Workup

  1. waitthe mixture left
  2. washwashed with 0.01N hydrochloric acid (2×50 ml)
  3. washThe organic phase was washed with saturated sodium hydrogencarbonate solution (50 ml), water (50 ml) and brine (50 ml)
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-00ec6ebb9a3a4907828742533f399212
Source dataset
uspto-grants-2003_11
Patent number
US06642229B2

Reaction notes

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