Ethyl Acetate → HCID 59636159, compound

HRID 80032Notes

Reaction equation

HRID 80032 reaction equation
Cl[CH2:2][CH2:3][CH2:4][NH:5][C:6]([NH:8][C:9]1[CH:10]=[N:11][CH:12]=[CH:13][CH:14]=1)=[O:7].[H-].[Na+].C(OCC)(=O)C>CN(C=O)C.C1COCC1>[N:11]1[CH:12]=[CH:13][CH:14]=[C:9]([N:8]2[CH2:2][CH2:3][CH2:4][NH:5][C:6]2=[O:7])[CH:10]=1

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 596362321-(3-Chloropropyl)-3-pyridin-3-ylurea

Product 1

HCID 59636159HCID 59636159, compoundYield 97.3%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

1-(3-Chloro-propyl)-3-pyridin-3-yl-urea (I-10a: 2.1 g, 9.859 mmol) in dry DMF (10 mL) was added to a solution of sodium hydride (487 mg, 10.154 mmol) in THF (2 mL) at 0° C. The reaction temperature was maintained at room temperature for 30 minutes. The reaction was monitored by TLC (100% ethyl acetate). The reaction mixture was quenched with MeOH (5 mL) at 0° C., concentrated under reduced pressure and partitioned between ice cold water and chloroform. The organic layer was dried over Na2SO4, and concentrated under reduced pressure to afford 1.7 g (97.14% yield) of 1-pyridin-3-yl-tetrahydro-pyrimidin-2-one.

Workup

  1. customThe reaction mixture was quenched with MeOH (5 mL) at 0° C.
  2. concentrationconcentrated under reduced pressure
  3. custompartitioned between ice cold water and chloroform
  4. dry with materialThe organic layer was dried over Na2SO4
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-1dcb5e71067742dfb6d66a417d9f7fe1
Source dataset
uspto-grants-2014_09
Patent number
USRE045173E1

Reaction notes

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