2-Butyn-1-ol → HCID 17979063, compound

HRID 1354123Notes

Reaction equation

HRID 1354123 reaction equation
[H-].[Na+].[Cl:3][C:4]([Cl:9])([Cl:8])[CH:5]([OH:7])[CH3:6].Cl[C:11]1[CH:16]=[C:15](Cl)[N:14]=[CH:13][N:12]=1.[CH2:18]([OH:22])[C:19]#[C:20][CH3:21].[Cl-].[NH4+]>O1CCCC1>[CH2:18]([O:22][C:11]1[CH:16]=[C:15]([O:7][CH:5]([CH3:6])[C:4]([Cl:9])([Cl:8])[Cl:3])[N:14]=[CH:13][N:12]=1)[C:19]#[C:20][CH3:21]

Participants

7

Reactant 5

HCID 129912-Butyn-1-olHCID 24758Sodium hydride2×HCID 25517Ammonium ChlorideHCID 661531,1,1-Trichloropropan-2-olHCID 709434,6-Dichloropyrimidine

Product 1

HCID 17979063HCID 17979063, compoundYield 70.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent4×

Procedure

In 4 ml of tetrahydrofuran was suspended 0.10 g of sodium hydride (60% in oil), to which 0.4 ml of a solution containing 0.33 g of 1,1,1-trichloro-2-propanol in tetrahydrofuran was added dropwise at 0° C., followed by stirring for 10 minutes. To this was added dropwise 0.4 ml of a solution containing 0.30 g of 4,6-dichloropyrimidine in tetrahydrofuran, followed by stirring at the same temperature for 35 minutes. To this was added dropwise 0.4 ml of a solution containing 0.16 g of 2-butyn-1-ol in tetrahydrofuran and further added 0.10 g of sodium hydride (60% in oil), followed by stirring at room temperature for 35 minutes. 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 0.44 g of 4-(2-butynyloxy)-6-(2,2,2-trichloro-1-methylethoxy)pyrimidine (the present compound (19)).

Workup

  1. additionwas added dropwise at 0° C.
  2. stirringby stirring at the same temperature for 35 minutes
  3. stirringby stirring at room temperature for 35 minutes
  4. extractionwas extracted three times with t-butyl methyl ether
  5. washThe combined organic layers were washed with a saturated aqueous sodium chloride solution
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-bdd67366ebc54e00aec239a990dd9d6d
Source dataset
uspto-grants-2007_05
Patent number
US07223769B2

Reaction notes

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