Lithium borohydride → HCID 21709156, compound

HRID 324974Notes

Reaction equation

HRID 324974 reaction equation
[C:1]1([C:7]2[N:12]=[C:11]([C:13](Cl)=[O:14])[CH:10]=[CH:9][N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[BH4-].[Li+]>O1CCCC1.C(OCC)(=O)C>[C:1]1([C:7]2[N:12]=[C:11]([CH2:13][OH:14])[CH:10]=[CH:9][N:8]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 2

HCID 4148881Lithium borohydrideHCID 541288844-Pyrimidinecarbonyl chloride, 2-phenyl-

Product 1

HCID 21709156HCID 21709156, compoundYield 81%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 145 mg of 2-phenyl-4-pyrimidinecarboxylic acid chloride in 5 mL tetrahydrofuran was added excess lithium borohydride. The reaction mixture was stirred at room temperature for 10 minutes then diluted with 25 mL of ethyl acetate and filtered. The filtrate was washed successively with 25 mL aliquots of 1 N sodium hydroxide and brine. The solvent was removed by evaporation under reduced pressure to yield 100 mg of 2-phenyl-4-hydroxymethylpyrimidine as a white solid.

Workup

  1. filtrationfiltered
  2. washThe filtrate was washed successively with 25 mL aliquots of 1 N sodium hydroxide and brine
  3. customThe solvent was removed by evaporation under reduced pressure

Sources & evidence

ORD record
ord-42b6410450854cf5964f5f4bbebb3b3b
Source dataset
uspto-grants-2001_04
Patent number
US06221871B1

Reaction notes

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