2-Butyn-1-ol → HCID 22599765, compound

HRID 1759908Notes

Reaction equation

HRID 1759908 reaction equation
[H-].[Na+].[CH2:3]([OH:7])[C:4]#[C:5][CH3:6].Cl[C:9]1[CH:14]=[C:13]([CH:15]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[F:23])[CH3:16])[N:12]=[CH:11][N:10]=1.[Cl-].[NH4+]>O1CCCC1>[CH2:3]([O:7][C:9]1[CH:14]=[C:13]([CH:15]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[F:23])[CH3:16])[N:12]=[CH:11][N:10]=1)[C:4]#[C:5][CH3:6]

Participants

6

Reactant 4

HCID 129912-Butyn-1-olHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 22599802HCID 22599802, compound

Product 1

HCID 22599765HCID 22599765, compoundYield 87.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

In 1 ml of tetrahydrofuran was suspended 0.02 g of sodium hydride (60% in oil), to which 0.3 ml of a tetrahydrofuran solution containing 0.02 g of 2-butyn-1-ol was slowly added dropwise with stirring at room temperature. The mixture was then stirred at room temperature for 20 minutes, to which 0.3 ml of a tetrahydrofuran solution containing 0.06 g of 4-chloro-6-(1-(2-fluorophenyl)ethyl)pyrimidine was slowly added dropwise at room temperature, followed by stirring for 4 hours. The reaction mixture was then poured into a saturated aqueous ammonium chloride solution and extracted three times with chloroform. The chloroform layers were combined, washed with water, dried over anhydrous magnesium sulfate, and then concentrated. The residue was subjected to silica gel column chromatography to give 0.06 g of 4-(2-butynyloxy)-6-(1-(2-fluorophenyl)ethyl)pyrimidine (the present compound (120)).

Workup

  1. additionwas slowly added dropwise
  2. additionwas slowly added dropwise at room temperature
  3. stirringby stirring for 4 hours
  4. extractionextracted three times with chloroform
  5. washwashed with water
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-5d51a067b84f4483bdfac73786426df7
Source dataset
uspto-grants-2005_01
Patent number
US06838463B2

Reaction notes

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