Propargyl alcohol → HCID 23324652, compound

HRID 1380833Notes

Reaction equation

HRID 1380833 reaction equation
[H-].[Na+].[CH2:3]([OH:6])[C:4]#[CH:5].[H][H].Cl[C:10]1[N:15]=[C:14]([CH:16]([CH3:18])[CH3:17])[N:13]=[C:12]([CH2:19][Cl:20])[CH:11]=1>CCCCC.O1CCCC1>[Cl:20][CH2:19][C:12]1[CH:11]=[C:10]([O:6][CH2:3][C:4]#[CH:5])[N:15]=[C:14]([CH:16]([CH3:18])[CH3:17])[N:13]=1

Participants

7

Reactant 4

HCID 7859Propargyl alcoholHCID 24758Sodium hydride3×HCID 23324650HCID 23324650, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 23324652HCID 23324652, compound

Reagents, catalysts & solvents 2

HCID 8003PentaneSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

21.5 g of 50% sodium hydride dispersion in oil (0.45 mol of NaH) are suspended briefly in 200 ml of absolute n-pentane under nitrogen. The sodium hydride is then liberated from the oil by decantation and covered with 400 ml of dry tetrahydrofuran. 25.4 ml (0.43 mol) of 2-propynol are then introduced while stirring well, the temperature of the mixture rising to 40° C. After completion of the hydrogen evolution the mixture is cooled to 0° C. and a solution of 6-chloro-4-chloromethyl-2-isopropyl-pyrimidine (see Example 61) in 100 ml of tetrahydrofuran is added dropwise during 30 minutes. The mixture is stirred for 16 hours and the major part of the solvent is then removed by evaporation under reduced pressure. The residue is subsequently taken up in 300 ml of methylene chloride and the solution is washed neutral twice with 300 ml of water each time. The organic phase is dried over anhydrous magnesium sulphate and concentrated and the reaction is purified on silica gel with diethyl ether/n-hexane (1:9). In this manner there is obtained 4-chloromethyl-2-isopropyl-6-(2-propynyloxy)-pyrimidine in the form of a yellowish oil, nD24 1.5142.

Workup

  1. customrising to 40° C
  2. stirringThe mixture is stirred for 16 hours
  3. customthe major part of the solvent is then removed by evaporation under reduced pressure
  4. washthe solution is washed neutral twice with 300 ml of water each time
  5. dry with materialThe organic phase is dried over anhydrous magnesium sulphate
  6. concentrationconcentrated
  7. customthe reaction is purified on silica gel with diethyl ether/n-hexane (1:9)

Sources & evidence

ORD record
ord-50b9390d2cd14d17a36f4051c28ec581
Source dataset
uspto-grants-1986_04
Patent number
US04584295

Reaction notes

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