5-(4-Formylphenyl)pyrimidine → (4-Pyrimidin-5-ylphenyl)methanol

HRID 1809165Notes

Reaction equation

HRID 1809165 reaction equation
[N:1]1[CH:6]=[C:5]([C:7]2[CH:14]=[CH:13][C:10]([CH:11]=[O:12])=[CH:9][CH:8]=2)[CH:4]=[N:3][CH:2]=1.[BH4-].[Na+]>CO>[N:1]1[CH:6]=[C:5]([C:7]2[CH:8]=[CH:9][C:10]([CH2:11][OH:12])=[CH:13][CH:14]=2)[CH:4]=[N:3][CH:2]=1

Participants

4

Reactant 2

HCID 38612125-(4-Formylphenyl)pyrimidineHCID 4311764Sodium borohydride2×

Product 1

HCID 7162046(4-Pyrimidin-5-ylphenyl)methanol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a 100 mL recovery flask was added 4-(5-pyrimidinyl)-benzaldehyde 48 (1.01 g, 5.49 mmol, 1.0 eq.) and CH3OH (30 mL). The resulting suspension was stirred upon which NaBH4 (311 mg, 8.23 mmol, 1.5 eq.) was added. Upon addition of NaBH4 the reaction became homogeneous. After stirring at room temperature for 2 h, the reaction was complete by LC/MS. The reaction mixture was concentrated and diluted with EtOAc upon which it was washed with a succession of water and brine. The aqueous phases were combined and extracted with EtOAc. The organic phases were dried over anhydrous Na2SO4, filtered, and concentrated to give a fine yellow powder that was used in subsequent reactions without further purification (523 mg, 51%).

Workup

  1. additionwas added
  2. concentrationThe reaction mixture was concentrated
  3. additiondiluted with EtOAc upon which it
  4. washwas washed with a succession of water and brine
  5. extractionextracted with EtOAc
  6. dry with materialThe organic phases were dried over anhydrous Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customto give a fine yellow powder that
  10. customwas used in subsequent reactions without further purification (523 mg, 51%)

Sources & evidence

ORD record
ord-278a6c1a754c4bc7a7f03227288b8f0d
Source dataset
uspto-grants-2013_01
Patent number
US08362017B2

Reaction notes

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