Sodium borohydride → 2-(4-Chloro-6-phenylpyrimidin-5-yl)ethanol

HRID 717580Notes

Reaction equation

HRID 717580 reaction equation
[Cl:1][C:2]1[C:7]([CH2:8][CH:9]=[O:10])=[C:6]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[N:5]=[CH:4][N:3]=1.[BH4-].[Na+]>CO>[Cl:1][C:2]1[C:7]([CH2:8][CH2:9][OH:10])=[C:6]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[N:5]=[CH:4][N:3]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 898150162-(4-Chloro-6-phenylpyrimidin-5-yl)acetaldehyde

Product 1

HCID 898153532-(4-Chloro-6-phenylpyrimidin-5-yl)ethanolYield 74.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of 2-(4-chloro-6-phenylpyrimidin-5-yl)acetaldehyde (450 mg) in dry methanol (10 mL), sodium borohydride (110 mg) was slowly added under nitrogen atmosphere at 0° C. The reaction mixture was stirred at room temperature for 2 hours and solvents were removed under reduced pressure. The resulting oil was diluted with dichloromethane (50 mL), washed with 10% NaHCO3 (10 mL) and brine (10 mL). The organic layer was dried over anhydrous Na2SO4 and concentrated to give a residue which was purified by column chromatography using MeOH/CHCl3 (0.2:9.8) as eluent to afford 2-(4-chloro-6-phenylpyrimidin-5-yl)ethanol (340 mg) as colorless oily liquid. 1H NMR (DMSO-d6): δ 2.89-2.94 (t, 2H), 3.53-3.58 (t, 2H), 4.81-4.85 (t, 1H), 7.50-7.61 (m, 5H), 8.92 (s, 1H).

Workup

  1. customsolvents were removed under reduced pressure
  2. additionThe resulting oil was diluted with dichloromethane (50 mL)
  3. washwashed with 10% NaHCO3 (10 mL) and brine (10 mL)
  4. dry with materialThe organic layer was dried over anhydrous Na2SO4
  5. concentrationconcentrated
  6. customto give a residue which
  7. customwas purified by column chromatography

Sources & evidence

ORD record
ord-18cdfc7b8f1d42d0babbb62674be5a4f
Source dataset
uspto-grants-2015_11
Patent number
US09193725B2

Reaction notes

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