2-Butyn-1-ol → HCID 17979084, compound

HRID 1354135Notes

Reaction equation

HRID 1354135 reaction equation
[H-].[Na+].[CH2:3]([OH:7])[C:4]#[C:5][CH3:6].Cl[C:9]1[CH:14]=[C:13]([O:15][CH2:16][C:17]2([CH3:22])[CH2:19][C:18]2([Cl:21])[Cl:20])[N:12]=[CH:11][N:10]=1.[Cl-].[NH4+]>O1CCCC1>[CH2:3]([O:7][C:9]1[CH:14]=[C:13]([O:15][CH2:16][C:17]2([CH3:22])[CH2:19][C:18]2([Cl:21])[Cl:20])[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 17979060HCID 17979060, compound

Product 1

HCID 17979084HCID 17979084, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

In 1.5 ml of tetrahydrofuran was suspended 0.04 g of sodium hydride (60% in oil), to which 0.3 ml of a solution containing 0.07 g of 2-butyn-1-ol was added dropwise at room temperature, followed by stirring for 10 minutes. To this was added dropwise 0.3 ml of a solution containing 0.23 g of 4-chloro-6-(2,2-dichloro-1-methylcyclopropylmethyloxy)pyrimidine in tetrahydrofuran at 0° C., followed by stirring at room temperature for 7 hours. The reaction mixture was then poured into a saturated aqueous ammonium chloride solution, which was extracted three times with t-butyl methyl ether. The combined organic layers were washed with a saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and then concentrated. The residue was subjected to silica gel column chromatography to give 0.22 g of 4-(2-butynyloxy)-6-(2,2-dichloro-1-methylcyclopropyl)methoxypyrimidine (the present compound (32)).

Workup

  1. additionwas added dropwise at room temperature
  2. stirringby stirring at room temperature for 7 hours
  3. extractionwas extracted three times with t-butyl methyl ether
  4. washThe combined organic layers were washed with a saturated aqueous sodium chloride solution
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-2e0dc94b9688455aba82ebba05daffc2
Source dataset
uspto-grants-2007_05
Patent number
US07223769B2

Reaction notes

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