Phosphorus oxychloride → 4-chloro-1-(4-methoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidine

HRID 1518311Notes

Reaction equation

HRID 1518311 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]2[C:13]3=[N:14][CH:15]=[N:16][C:17](=O)[CH:12]3[CH:11]=[N:10]2)=[CH:5][CH:4]=1.P(Cl)(Cl)([Cl:21])=O>>[Cl:21][C:17]1[N:16]=[CH:15][N:14]=[C:13]2[N:9]([C:6]3[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=3)[N:10]=[CH:11][C:12]=12

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 594475481-(4-methoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4(3aH)-one

Product 1

HCID 20493134-chloro-1-(4-methoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidine

Conditions

Temperature
100 °C

Procedure

A mixture of compound 44B (2 g, 8.26 mmol) and phosphoryl trichloride (11.51 mL, 124 mmol) was heated at 100° C. for 2 h and cooled. The reaction mixture was slowly poured onto ice. The precipitate was collected, washed with water and dried to provide the desired product. MS (APCI): m/z 261 (M+H).

Workup

  1. temperaturecooled
  2. additionThe reaction mixture was slowly poured onto ice
  3. customThe precipitate was collected
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-9c858c8113104c05911d75f837a0bf99
Source dataset
uspto-grants-2012_07
Patent number
US08232273B2

Reaction notes

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