Phosphorus oxychloride → HCID 57504741, compound

HRID 1098279Notes

Reaction equation

HRID 1098279 reaction equation
P(Cl)(Cl)([Cl:3])=O.[Cl:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([F:13])[C:8]=1[N:14]1[C:18]2=[N:19][CH:20]=[N:21][C:22](O)=[C:17]2[CH:16]=[N:15]1>>[Cl:3][C:22]1[N:21]=[CH:20][N:19]=[C:18]2[N:14]([C:8]3[C:9]([F:13])=[CH:10][CH:11]=[CH:12][C:7]=3[Cl:6])[N:15]=[CH:16][C:17]=12

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178517922HCID 178517922, compound

Product 1

HCID 57504741HCID 57504741, compoundYield 93.1%

Conditions

Temperature
100 °C

Procedure

Phosphorus oxychloride (17.54 mL, 188.18 mmol) was added to 1-(2-chloro-6-fluorophenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-ol (Intermediate BH2) (2.49 g, 9.41 mmol). The resulting solution was stirred at 100° C. for 1 hour. The reaction mixture was evaporated. Ice/water (100 mL) and then EtOAc (100 mL) were added. The organic layer was separated and the aqueous layer re-extracted with EtOAc (100 mL). The combined organics were washed with water (100 mL), dried (MgSO4) and concentrated to give the crude product (2.48 g) which was used without further purification.

Workup

  1. customThe reaction mixture was evaporated
  2. additionIce/water (100 mL) and then EtOAc (100 mL) were added
  3. customThe organic layer was separated
  4. extractionthe aqueous layer re-extracted with EtOAc (100 mL)
  5. washThe combined organics were washed with water (100 mL)
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-38dc1ae9f5bf481eab885810a6781b99
Source dataset
uspto-grants-2012_03
Patent number
US08143263B2

Reaction notes

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