Sodium borohydride → HCID 57936308, compound

HRID 1434916Notes

Reaction equation

HRID 1434916 reaction equation
[BH4-].[Na+].[CH3:3][S:4][C:5]1[N:10]=[C:9]([C:11]2[S:15][C:14](/[CH:16]=[CH:17]/[C:18](=[O:20])[CH3:19])=[CH:13][CH:12]=2)[CH:8]=[CH:7][N:6]=1>CO>[CH3:3][S:4][C:5]1[N:10]=[C:9]([C:11]2[S:15][C:14](/[CH:16]=[CH:17]/[CH:18]([OH:20])[CH3:19])=[CH:13][CH:12]=2)[CH:8]=[CH:7][N:6]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 57936158HCID 57936158, compound

Product 1

HCID 57936308HCID 57936308, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Solid sodium borohydride (25 mg, 0.66 mmol) was added to a solution of (E)-4-[5-(2-methylsulfanyl-pyrimidin-4-yl)-thiophen-2-yl]-but-3-en-2-one (120 mg, 0.43 mmol) in 8 ml of MeOH. After stirring for 3 hours, the MeOH was evaporated and the residue was partitioned between water and EtOAc. The aqueous layer was separated and extracted once more with EtOAc. The combined organic extracts were washed with brine, dried over sodium sulfate and evaporated to give a yellow solid which was used without further purification. Yield: 112 mg (93%).

Workup

  1. customthe MeOH was evaporated
  2. customthe residue was partitioned between water and EtOAc
  3. customThe aqueous layer was separated
  4. extractionextracted once more with EtOAc
  5. washThe combined organic extracts were washed with brine
  6. dry with materialdried over sodium sulfate
  7. customevaporated
  8. customto give a yellow solid which
  9. customwas used without further purification

Sources & evidence

ORD record
ord-05adeb231d7143959b62c4c624c83c79
Source dataset
uspto-grants-2009_11
Patent number
US07615562B2

Reaction notes

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