Thionyl Chloride → HCID 178448669, compound

HRID 621473Notes

Reaction equation

HRID 621473 reaction equation
[CH2:1]([N:5]1[C:10](=[O:11])[C:9]2[C:12]([NH:15][CH3:16])=[N:13][NH:14][C:8]=2[N:7]([CH2:17][CH2:18]O)[C:6]1=[O:20])[CH2:2][CH2:3][CH3:4].S(Cl)([Cl:23])=O>C(Cl)(Cl)Cl.N1C=CC=CC=1>[CH2:1]([N:5]1[C:10](=[O:11])[C:9]2[C:12]([NH:15][CH3:16])=[N:13][NH:14][C:8]=2[N:7]([CH2:17][CH2:18][Cl:23])[C:6]1=[O:20])[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 2

HCID 24386Thionyl ChlorideHCID 178448671HCID 178448671, compound

Product 1

HCID 178448669HCID 178448669, compoundYield 94%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6212ChloroformSolvent

Procedure

To a suspension of 5-butyl-7-(2-hydroxyethyl)-3-methylaminopyrazolo[3,4-d]pyrimidine-4,6(5H,7H)-dione (2.5 g, 8.9 mM) in chloroform (30 ml) and pyridine (4 ml, 50 mM) was added thionyl chloride (3,7 ml, 50 mM) at room temperature. The solution was refluxed for 2 hours and concentrated to dryness under reduced pressure to give a syrup. The syrup was poured onto ice-water to give colorless powder. Recrystallization from DMF/methanol/water gave colorless crystals (2.5 g, 94%), m.p. 270°-272° C.

Workup

  1. temperatureThe solution was refluxed for 2 hours
  2. concentrationconcentrated to dryness under reduced pressure
  3. customto give a syrup
  4. additionThe syrup was poured onto ice-water
  5. customto give colorless powder
  6. customRecrystallization from DMF/methanol/water

Sources & evidence

ORD record
ord-a460801b547f45ca9076a43acf936c2a
Source dataset
uspto-grants-1989_04
Patent number
US04824848

Reaction notes

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