Sodium borohydride → HCID 86094281, compound

HRID 2099580Notes

Reaction equation

HRID 2099580 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([C:8]([C:10]2[CH:11]=[C:12]([CH:15]=[CH:16][CH:17]=2)[C:13]#[N:14])=[O:9])[CH:5]=[CH:4][N:3]=1.[BH4-].[Na+]>CO.C(Cl)Cl>[Cl:1][C:2]1[N:7]=[C:6]([CH:8]([OH:9])[C:10]2[CH:11]=[C:12]([CH:15]=[CH:16][CH:17]=2)[C:13]#[N:14])[CH:5]=[CH:4][N:3]=1

Participants

5

Reactant 2

HCID 4311764Sodium borohydride2×HCID 86094278HCID 86094278, compound

Product 1

HCID 86094281HCID 86094281, compoundYield 96%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent3×HCID 6344DichloromethaneSolvent

Procedure

3-[(2-chloropyrimidin-4-yl)carbonyl]benzonitrile (3 g, 12.31 mmol) was dissolved in 90 mL dry methanol and cooled to 0 C. Sodium borohydride (Acros, 0.512 g, 13.54 mmol) was dissolved in 30 mL dry methanol and added slowly via syringe, and the reaction mixture stirred at 0 C for 100 min. Additional sodium borohydride (0.256 g, 6.77 mmol) was dissolved in 15 mL dry methanol and added via syringe. After 20 minutes the reaction mixture was diluted with methylene chloride and quenched with saturated sodium bicarbonate. The resulting mixture was partitioned between methylene chloride and saturated sodium bicarbonate. The aqueous portion was extracted with methylene chloride (3×), and the combined organic portion dried over sodium sulfate and concentrated in vacuo to give 3-[(2-chloropyrimidin-4-yl)(hydroxy)methyl]benzonitrile (2.9 g, 96%). LRMS m/z (M+H) Calcd: 246.7, found: 246.0.

Workup

  1. temperaturecooled to 0 C
  2. additionadded slowly via syringe
  3. additionadded via syringe
  4. customquenched with saturated sodium bicarbonate
  5. customThe resulting mixture was partitioned between methylene chloride and saturated sodium bicarbonate
  6. extractionThe aqueous portion was extracted with methylene chloride (3×)
  7. dry with materialthe combined organic portion dried over sodium sulfate
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-b1fdf4caa3f948009f12bbd874d94c29
Source dataset
uspto-grants-2009_08
Patent number
US07569589B2

Reaction notes

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