Phosphorus oxychloride → HCID 57504679, compound

HRID 1098209Notes

Reaction equation

HRID 1098209 reaction equation
P(Cl)(Cl)([Cl:3])=O.O[C:7]1[N:12]=[CH:11][N:10]=[C:9]2[N:13]([C:16]3[CH:17]=[C:18]([CH:21]=[CH:22][C:23]=3[CH3:24])[C:19]#[N:20])[N:14]=[CH:15][C:8]=12>>[Cl:3][C:7]1[N:12]=[CH:11][N:10]=[C:9]2[N:13]([C:16]3[CH:17]=[C:18]([CH:21]=[CH:22][C:23]=3[CH3:24])[C:19]#[N:20])[N:14]=[CH:15][C:8]=12

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178425531HCID 178425531, compound

Product 1

HCID 57504679HCID 57504679, compoundYield 90%

Conditions

Temperature
100 °C

Procedure

Phosphorus oxychloride (8.90 mL, 95.52 mmol) was added to 3-(4-hydroxy-1H-pyrazolo[3,4-d]pyrimidin-1-yl)-4-methylbenzonitrile (Intermediate AM3) (1.2 g, 4.78 mmol). The resulting solution was stirred at 100° C. for 4 hours. The reaction mixture was evaporated and then azetroped with toluene to remove any residual POCl3. Ice/water was added and the formed precipitate was filtered washing well with water and dried overnight in vacuo over P2O5 to afford 3-(4-chloro-1H-pyrazolo[3,4-d]pyrimidin-1-yl)-4-methylbenzonitrile (1.16 g, 90%). 1H NMR (400 MHz, DMSO) 2.21 (3H, s), 7.73 (1H, d), 7.97-8.00 (1H, m), 8.06 (1H, d), 8.81 (1H, s), 8.91 (1H, s); HPLC tR=2.05 min.

Workup

  1. customThe reaction mixture was evaporated
  2. customto remove any residual POCl3
  3. additionIce/water was added
  4. filtrationthe formed precipitate was filtered
  5. washwashing well with water
  6. dry with materialdried overnight in vacuo over P2O5

Sources & evidence

ORD record
ord-b41dd03c3cb44be68f47c1ec7ff6c6dc
Source dataset
uspto-grants-2012_03
Patent number
US08143263B2

Reaction notes

Loading…