2-Butyn-1-ol → HCID 69427931, compound

HRID 1759942Notes

Reaction equation

HRID 1759942 reaction equation
[H-].[Na+].[CH2:3]([OH:7])[C:4]#[C:5][CH3:6].Cl[C:9]1[CH:14]=[C:13]([O:15][C@@H:16]2[CH2:20][CH2:19][CH2:18][C@H:17]2[CH3:21])[N:12]=[CH:11][N:10]=1.[Cl-].[NH4+]>O1CCCC1>[CH2:3]([O:7][C:9]1[CH:14]=[C:13]([O:15][C@@H:16]2[CH2:20][CH2:19][CH2:18][C@H:17]2[CH3:21])[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 86591869HCID 86591869, compound

Product 1

HCID 69427931HCID 69427931, compoundYield 81.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

In 3.6 ml of tetrahydrofuran was suspended 0.09 g of sodium hydride (60% in oil), to which 0.6 ml of a tetrahydrofuran solution containing 0.14 g of 2-butyn-1-ol was slowly added dropwise under stirring at room temperature. The mixture was stirred at room temperature for 20 minutes, and 0.6 ml of a tetrahydrofuran solution containing 0.38 g of 4-chloro-6-(trans-2-methylcyclopentyloxy)pyrimidine was slowly added dropwise, followed by stirring at room temperature for 3 hours. The reaction mixture was then poured into a saturated aqueous ammonium chloride solution and extracted three times with ethyl acetate. The organic 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 0.36 g of 4-(2-butynyloxy)-6-(trans-2-methylcyclopentyloxy)pyrimidine (the present compound (169)).

Workup

  1. additionwas slowly added dropwise
  2. stirringThe mixture was stirred at room temperature for 20 minutes
  3. additionwas slowly added dropwise
  4. stirringby stirring at room temperature for 3 hours
  5. extractionextracted three times with ethyl acetate
  6. washwashed with water
  7. dry with materialdried over anhydrous magnesium sulfate
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-3683ba3ed96743adb9a4770179536b39
Source dataset
uspto-grants-2005_01
Patent number
US06838463B2

Reaction notes

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