Lithium borohydride → HCID 21709156, compound

HRID 651725Notes

Reaction equation

HRID 651725 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 1N 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 1N sodium hydroxide and brine
  3. customThe solvent was removed by evaporation under reduced pressure

Sources & evidence

ORD record
ord-8e839fb903554cbab9405789debc2259
Source dataset
uspto-grants-2001_08
Patent number
US06281359B1

Reaction notes

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