Water → HCID 22599778, compound

HRID 1759826Notes

Reaction equation

HRID 1759826 reaction equation
Cl[C:2]1[CH:7]=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[N:5]=[CH:4][N:3]=1.[CH2:14]([OH:17])[C:15]#[CH:16].[H-].[Na+].O>O1CCCC1>[C:8]1([C:6]2[CH:7]=[C:2]([O:17][CH2:14][C:15]#[CH:16])[N:3]=[CH:4][N:5]=2)[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7859Propargyl alcoholHCID 24758Sodium hydrideHCID 5934294-Chloro-6-phenylpyrimidine

Product 1

HCID 22599778HCID 22599778, compoundYield 88.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In 5 ml of tetrahydrofuran were dissolved 194 mg of 4-chloro-6-phenylpyrimidine and 68 mg of 2-propyn-1-ol, to which 50 mg of sodium hydride (60% in oil) was added with stirring at room temperature, followed by further stirring for 3 hours. The reaction mixture was then poured into water and extracted with ethyl acetate. The organic layer was washed with a saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and then concentrated. The resulting residue was subjected to silica gel column chromatography to give 190 mg of 4-phenyl-6-(2-propynyloxy)pyrimidine (the present compound (37)), m.p.: 65.1° C.

Workup

  1. stirringby further stirring for 3 hours
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with a saturated aqueous sodium chloride solution
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-9f23a378ec5943f382eb2489d4ca7921
Source dataset
uspto-grants-2005_01
Patent number
US06838463B2

Reaction notes

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