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

HRID 1796099Notes

Reaction equation

HRID 1796099 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-00aac1a9b02d4dee9b1e1b6bc23989d5
Source dataset
uspto-grants-2006_04
Patent number
US07030128B2

Reaction notes

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