Phosphorus oxychloride → HCID 57438671, compound

HRID 1098274Notes

Reaction equation

HRID 1098274 reaction equation
P(Cl)(Cl)([Cl:3])=O.[CH3:6][C:7]1[C:8]([N:12]2[C:16]3=[N:17][CH:18]=[N:19][C:20](O)=[C:15]3[CH:14]=[N:13]2)=[CH:9][S:10][CH:11]=1>>[Cl:3][C:20]1[N:19]=[CH:18][N:17]=[C:16]2[N:12]([C:8]3[C:7]([CH3:6])=[CH:11][S:10][CH:9]=3)[N:13]=[CH:14][C:15]=12

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178431885HCID 178431885, compound

Product 1

HCID 57438671HCID 57438671, compoundYield 93%

Conditions

Temperature
100 °C

Procedure

Phosphoryl trichloride (4.2 mL, 45 mmol) was added in one portion to 1-(4-methylthiophen-3-yl)-1H-pyrazolo[3,4-d]pyrimidin-4-ol (Intermediate BF2) (700 mg, 3.01 mmol). The resulting suspension was heated to 100° C. to give a solution and stirred for 2 hours. The mixture was evaporated and ice added to the residue and stirred for 30 minutes. It was then filtered and the solids washed with water (3×10 mL). The crude product was dissolved in ethyl acetate (40 mL), dried with MgSO4, filtered and evaporated to give the product (700 mg, 93%).

Workup

  1. customto give a solution
  2. customThe mixture was evaporated
  3. additionice added to the residue
  4. stirringstirred for 30 minutes
  5. filtrationIt was then filtered
  6. washthe solids washed with water (3×10 mL)
  7. dissolutionThe crude product was dissolved in ethyl acetate (40 mL)
  8. dry with materialdried with MgSO4
  9. filtrationfiltered
  10. customevaporated

Sources & evidence

ORD record
ord-b7195ec4bf0d49feb57c63f599e880e7
Source dataset
uspto-grants-2012_03
Patent number
US08143263B2

Reaction notes

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