Chloroform → 5-Benzyloxymethyl-7-chloro-6-(2-chloroethyl)pyrazolo[1,5-a]pyrimidine

HRID 1106537Notes

Reaction equation

HRID 1106537 reaction equation
[CH2:1]([O:8][CH2:9][C:10]1[NH:11][C:12]2[N:13]([N:20]=[CH:21][CH:22]=2)C(=O)[C:15]=1[CH2:16][CH2:17]O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.P(Cl)(Cl)([Cl:25])=O.C(N(CC)CC)C.[CH:35]([Cl:38])(Cl)Cl>>[CH2:1]([O:8][CH2:9][C:10]1[C:15]([CH2:16][CH2:17][Cl:25])=[C:35]([Cl:38])[N:13]2[N:20]=[CH:21][CH:22]=[C:12]2[N:11]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 4

HCID 6212ChloroformHCID 8471TriethylamineHCID 24813Phosphorus oxychlorideHCID 178516281HCID 178516281, compound

Product 1

HCID 187890955-Benzyloxymethyl-7-chloro-6-(2-chloroethyl)pyrazolo[1,5-a]pyrimidineYield 63.4%

Conditions

Temperature
105 °C

Procedure

To 0.52 g of 5-benzyloxymethyl-6-(2-hydroxy-ethyl)pyrazolo[1,5-a]pyrimidin-7(4H)-one were added 4.0 ml of phosphorus oxychloride and 0.55 ml of triethylamine, and the mixture was stirred for 1 hour and 20 minutes in an oil bath heated to 100-110° C. Excess phosphorus oxychloride was distilled off under reduced pressure, and the residue was poured into ice water and extracted with chloroform. After the chloroform layer was dried over anhydrous sodium sulfate, the solvent was distilled off under reduced pressure. The thus-obtained crude product was subjected to column chromatography on silica gel (elution solvent: chloroform alone) to obtain 0.37 g (yield: 63.4%) of the intended product.

Workup

  1. distillationExcess phosphorus oxychloride was distilled off under reduced pressure
  2. additionthe residue was poured into ice water
  3. extractionextracted with chloroform
  4. dry with materialAfter the chloroform layer was dried over anhydrous sodium sulfate
  5. distillationthe solvent was distilled off under reduced pressure
  6. customThe thus-obtained crude product
  7. washelution solvent

Sources & evidence

ORD record
ord-59a5e6820998461487dc76e782de0dca
Source dataset
uspto-grants-2000_05
Patent number
US06057330

Reaction notes

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