Chloride → HCID 22241378, compound

HRID 892137Notes

Reaction equation

HRID 892137 reaction equation
[H-].[Na+].[OH:3][C:4]1[CH:5]=[C:6]([CH:9]=[CH:10][CH:11]=1)[C:7]#[N:8].[Cl-].CN1[C:19](=[O:20])N(C)CCC1.C1[CH2:26][O:25][CH2:24][CH2:23]1>>[CH3:26][O:25][CH2:24][CH2:23][O:3][C:4]1[C:5]([O:20][CH3:19])=[C:6]([CH:9]=[CH:10][CH:11]=1)[C:7]#[N:8]

Participants

6

Reactant 5

HCID 312ChlorideHCID 8028Tetrahydrofuran2×HCID 133943-CyanophenolHCID 24758Sodium hydrideHCID 816462(1H)-Pyrimidinone, tetrahydro-1,3-dimethyl-

Product 1

HCID 22241378HCID 22241378, compound

Procedure

To a cooled (0° C.) suspension of sodium hydride (840 mg, 60% dispersion in mineral oil, 21 mmol) in THF (20 mL) is added a solution comprising 3-hydroxy-benzonitrile (2.4 g, 20 mmol), MEM Chloride (2.25 mL, 20 mmol) and DMPU (2 mL) in THF (20 mL). On complete addition, the cold bath is removed and stirring continued for 3 h. The reaction mixture is then diluted with ether, washed with water and brine, dried over MgSO4 and concentrated. The residue is purified by flash chromatography (silica, 30% ethyl acetate 10% dichloromethane in hexane) to give the title compound as an oil. MS (ESI) 207 (M+H)+.

Workup

  1. temperatureTo a cooled
  2. additionOn complete addition
  3. customthe cold bath is removed
  4. additionThe reaction mixture is then diluted with ether
  5. washwashed with water and brine
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated
  8. customThe residue is purified by flash chromatography (silica, 30% ethyl acetate 10% dichloromethane in hexane)

Sources & evidence

ORD record
ord-f184a8bdd58646b4bb97cc7a491dd73a
Source dataset
uspto-grants-2006_02
Patent number
US07005440B1

Reaction notes

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