Sodium triacetoxyborohydride → Imidazo[1,2-a]pyrimidin-7-ylmethanol

HRID 478230Notes

Reaction equation

HRID 478230 reaction equation
C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[N:15]1[CH:16]=[CH:17][N:18]2[CH:23]=[CH:22][C:21]([CH:24]=[O:25])=[N:20][C:19]=12>CO>[N:15]1[CH:16]=[CH:17][N:18]2[CH:23]=[CH:22][C:21]([CH2:24][OH:25])=[N:20][C:19]=12

Participants

4

Reactant 2

HCID 5049666Sodium triacetoxyborohydrideHCID 18001283Imidazo[1,2-A]pyrimidine-7-carbaldehyde

Product 1

HCID 18001293Imidazo[1,2-a]pyrimidin-7-ylmethanolYield 99.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Sodium triacetoxyborohydride (21.5 g, 102 mmol) was added portionwise over 20 min to a stirred solution of imidazo[1,2-a]pyrimidine-7-carbaldehyde (5.00 g, 34.0 mmol) in methanol (100 ml) and the solution left to stir at ambient temperature for 18 h. The solvent was evaporated, the residue redissolved in methanol (150 ml) and pre-adsorbed onto silica. Purification by chromatography on silica gel eluting with dichloromethane (containing 1% conc. ammonia) on a gradient of methanol (1-10%) gave imidazo[1,2-a]pyrimidin-7-ylmethanol (5.06 g, 99%) as a white solid: δH (360 MHz, DMSO) 4.57 (2H, d, J 6), 5.62 (1H, t, J 6), 7.13 (1H, d, J 7), 7.64 (1H, d, J 1), 7.86 (1H, d, J 1), 8.94 (1H, d, J 7).

Workup

  1. waitthe solution left
  2. customThe solvent was evaporated
  3. dissolutionthe residue redissolved in methanol (150 ml) and pre-adsorbed onto silica
  4. customPurification by chromatography on silica gel eluting with dichloromethane (containing 1% conc. ammonia) on a gradient of methanol (1-10%)

Sources & evidence

ORD record
ord-cc5392ea746a46389e0dfc24d9a7e783
Source dataset
uspto-grants-2003_11
Patent number
US06642229B2

Reaction notes

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