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

HRID 2183878Notes

Reaction equation

HRID 2183878 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-α]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-α]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-54c683e473924bf4a7a66fab3872d54c
Source dataset
uspto-grants-2005_05
Patent number
US06900215B2

Reaction notes

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