Sodium hydride → HCID 117770681, compound

HRID 1526285Notes

Reaction equation

HRID 1526285 reaction equation
Cl[C:2]1[CH:7]=[C:6]([Cl:8])[N:5]=[CH:4][N:3]=1.[OH:9][CH2:10][CH2:11][N:12]1[CH2:16][CH2:15][CH2:14][C:13]1=[O:17].[H-].[Na+].[Cl-].[NH4+]>CN(C)C=O.O>[Cl:8][C:6]1[N:5]=[CH:4][N:3]=[C:2]([O:9][CH2:10][CH2:11][N:12]2[CH2:16][CH2:15][CH2:14][C:13]2=[O:17])[CH:7]=1

Participants

7

Reactant 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 709434,6-DichloropyrimidineHCID 769801-(2-Hydroxyethyl)-2-pyrrolidinone

Product 1

HCID 117770681HCID 117770681, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 4,6-dichloropyrimidine (600 mg) and 1-(2-hydroxyethyl)-2-pyrrolidinone (0.728 mL) in N,N-dimethylformamide (2 mL) was added sodium hydride (60% oil, 209 mg) under ice-cooling, and the mixture was stirred for 30 min. The reaction mixture was poured into saturated aqueous ammonium chloride solution (10 mL), water (5 mL) was added thereto, and the mixture was extracted with ethyl acetate. The organic layer was washed with, water (10 mL, threetimes) and saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The obtained pale-yellow oil was purified by silica gel chromatography (hexane/ethyl acetate) to give the title compound (634 mg).

Workup

  1. temperaturecooling
  2. additionwas added
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with, water (10 mL, threetimes) and saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customthe solvent was evaporated under reduced pressure
  7. customThe obtained pale-yellow oil was purified by silica gel chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-cee829f39729407f9f3d2ba55cd4c380
Source dataset
uspto-grants-2015_07
Patent number
US09085578B2

Reaction notes

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