Sodium borohydride → HCID 67342731, compound

HRID 1669270Notes

Reaction equation

HRID 1669270 reaction equation
[F:1][C:2]([F:24])([F:23])[C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:14]=[CH:13][C:12]([C:15](=[O:22])[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])=[CH:11][N:10]=2)=[CH:5][CH:4]=1.[BH4-].[Na+]>C(O)C>[F:24][C:2]([F:1])([F:23])[C:3]1[CH:4]=[CH:5][C:6]([C:9]2[N:10]=[CH:11][C:12]([CH:15]([OH:22])[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])=[CH:13][N:14]=2)=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 67342066HCID 67342066, compound

Product 1

HCID 67342731HCID 67342731, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
0 °C

Procedure

1-[2-(4-Trifluoromethyl-phenyl)-pyrimidin-5-yl]-heptan-1-one (1.47 g, 4.36 mmol) is dissolved in ethanol and cooled to 0° C. while stirring under nitrogen. To the flask is added sodium borohydride (165 mg, 4.36 mmol), and the reaction is kept at 0° C. for 1 h., then slowly warmed to room temperature. The reaction is monitored by HPLC. Upon complete consumption of starting material, the reaction is carefully quenched with water, the ethanol removed by rotary evaporator, and extracted with diethyl ether, washed, dried, and concentrated. The title compound is used in the next step without further purification.

Workup

  1. temperatureslowly warmed to room temperature
  2. customUpon complete consumption of starting material
  3. customthe reaction is carefully quenched with water
  4. customthe ethanol removed by rotary evaporator
  5. extractionextracted with diethyl ether
  6. washwashed
  7. customdried
  8. concentrationconcentrated
  9. customThe title compound is used in the next step without further purification

Sources & evidence

ORD record
ord-140af3cfd7d54359a338f149a0d8ac03
Source dataset
uspto-grants-2011_08
Patent number
US07989457B2

Reaction notes

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