Glycidol → HCID 86713094, compound

HRID 1774311Notes

Reaction equation

HRID 1774311 reaction equation
[NH:1]1[CH:6]=[CH:5][CH:4]=[N:3][C:2]1=[O:7].[CH2:8]1[O:10][CH:9]1[CH2:11]O.[H-].[Na+]>CN(C=O)C.[Cl-].[Na+].O>[O:10]1[CH2:8][CH:9]1[CH2:11][O:7][C:2]1[N:1]=[CH:6][CH:5]=[CH:4][N:3]=1

Participants

6

Reactant 3

HCID 11164GlycidolHCID 24758Sodium hydrideHCID 684012(1H)-Pyrimidinone

Product 1

HCID 86713094HCID 86713094, compoundYield 30%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 57417360Sodium chloride; waterSolvent

Procedure

A solution of 2 (1H)-pyrimidinone (0.61 g, 4 mmol) and glycidol (0.30 g, 4 mmol) in DMF (10 mL) was added dropwise to a stirred suspension of NaH (0.14 g, 6 mmol) in DMF (5 mL). The reaction mixture is stirred at r. t. until the reagents disappeared (TLC). The reaction mixture is taken up with brine and extracted with EtOAc (3×20 mL). The organic phases are separated, dried over Na2SO4 and evaporated under reduced pressure. The crude residue was chromatographed (Petroleum ether/AcOEt, 1:1, as eluent) to afford pure compound in 30% yield. 1H NMR (CDCl3): δ 2.60-2.70 (m, 2H), 3.16 (m, 1H), 3.89-4.04 (m, 2H), 4.17-4.28 (m, 1H), 4.50-4.65 (m, 1H), 7.00 (t, 1H, J=7.4 Hz), 8.56 (d, 2H, J=4.9 Hz).

Workup

  1. extractionextracted with EtOAc (3×20 mL)
  2. customThe organic phases are separated
  3. dry with materialdried over Na2SO4
  4. customevaporated under reduced pressure
  5. customThe crude residue was chromatographed (Petroleum ether/AcOEt, 1:1, as eluent)
  6. customto afford pure compound in 30% yield

Sources & evidence

ORD record
ord-61ea3afe8bb44b7eb569ac99f682da38
Source dataset
uspto-grants-2016_02
Patent number
US09260400B2

Reaction notes

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