Ethanol → HCID 67958818, compound

HRID 707643Notes

Reaction equation

HRID 707643 reaction equation
C([O:3][C:4]([C:6]1[CH:10]=[C:9]([C:11]2[N:16]=[CH:15][CH:14]=[CH:13][N:12]=2)[O:8][N:7]=1)=O)C.C(O)C.[BH4-].[Na+]>C1COCC1>[OH:3][CH2:4][C:6]1[CH:10]=[C:9]([C:11]2[N:16]=[CH:15][CH:14]=[CH:13][N:12]=2)[O:8][N:7]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 4311764Sodium borohydrideHCID 67958876HCID 67958876, compound

Product 1

HCID 67958818HCID 67958818, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
30 °C

Procedure

To a mixture of 2-(3-ethoxycarbonyl-isoxazol-5-yl)-pyrimidine (35 gm) in 2:1 v/v ethanol:THF mixture (525 ml) was added sodium borohydride (7.5 gm) in lots at 0° C. It was stirred at 30° C. temperature over a period of 4 h. The reaction mixture was evaporated under vacuum to provide a residue and to the residue, (150 ml) was added. The suspension was extracted with ethyl acetate (4.5 ltr). Combined organic layers was washed with water and concentrated under vacuum to provide crude mass in 23 gm quantity, which was recrystallized from ethanol to provide the title compound in 15.1 gm quantity (53%) as pale yellow solid.

Workup

  1. customThe reaction mixture was evaporated under vacuum
  2. customto provide a residue
  3. additionto the residue, (150 ml) was added
  4. extractionThe suspension was extracted with ethyl acetate (4.5 ltr)
  5. washCombined organic layers was washed with water
  6. concentrationconcentrated under vacuum
  7. customto provide crude mass in 23 gm quantity, which
  8. customwas recrystallized from ethanol

Sources & evidence

ORD record
ord-56298a5c683745fb9d0a54806effde38
Source dataset
uspto-grants-2015_11
Patent number
US09175031B2

Reaction notes

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