Sodium hydride → HCID 17979116, compound

HRID 1354140Notes

Reaction equation

HRID 1354140 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:23])[C:19]#[C:20][CH2:21][CH3:22].[Cl-].[NH4+]>O1CCCC1>[CH2:18]([O:23][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][CH2:21][CH3:22]

Participants

7

Reactant 5

HCID 24758Sodium hydride2×HCID 25517Ammonium ChlorideHCID 661531,1,1-Trichloropropan-2-olHCID 709434,6-DichloropyrimidineHCID 804212-Pentyn-1-ol

Product 1

HCID 17979116HCID 17979116, compoundYield 72.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

In 3 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 3,3,3-trichloro-2-propanol was added dropwise at room temperature, followed by stirring for 10 minutes. To this was added dropwise 0.4 ml of a solution containing 0.3 g of 4,6-dichloropyrimidine in tetrahydrofuran at 0° C., followed by stirring at the same temperature for 30 minutes. To this was added dropwise 0.4 ml of a solution containing 0.20 g of 2-pentyn-1-ol at room temperature and further added 0.10 g of sodium hydride (60% in oil), followed by stirring for 2 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 0.47 g of 4-(2-pentynyloxy)-6-(2,2,2-trichloro-1-methylethoxy)pyrimidine (the present compound (38)).

Workup

  1. additionwas added dropwise at room temperature
  2. stirringby stirring at the same temperature for 30 minutes
  3. stirringby stirring for 2 hours
  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-42246f19d4f244c39503559846c0e700
Source dataset
uspto-grants-2007_05
Patent number
US07223769B2

Reaction notes

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