Phosphorus oxychloride → 3-chloro-2-(4-chloro-1H-pyrazolo[3,4-d]pyrimidin-1-yl)benzonitrile

HRID 655723Notes

Reaction equation

HRID 655723 reaction equation
P(Cl)(Cl)([Cl:3])=O.[Cl:6][C:7]1[C:8]([N:15]2[C:19]3=[N:20][CH:21]=[N:22][C:23](O)=[C:18]3[CH:17]=[N:16]2)=[C:9]([CH:12]=[CH:13][CH:14]=1)[C:10]#[N:11]>>[Cl:6][C:7]1[C:8]([N:15]2[C:19]3=[N:20][CH:21]=[N:22][C:23]([Cl:3])=[C:18]3[CH:17]=[N:16]2)=[C:9]([CH:12]=[CH:13][CH:14]=1)[C:10]#[N:11]

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178509758HCID 178509758, compound

Product 1

HCID 575045663-chloro-2-(4-chloro-1H-pyrazolo[3,4-d]pyrimidin-1-yl)benzonitrileYield 75.3%

Conditions

Temperature
100 °C

Procedure

Phosphorus oxychloride (7.93 mL, 85.03 mmol) was added to 3-chloro-2-(4-hydroxy-1H-pyrazolo[3,4-d]pyrimidin-1-yl)benzonitrile (Intermediate AH5) (1.155 g, 4.25 mmol). The resulting mixture was heated to 100° C. and stirred for 4 hours. The reaction mixture was allowed to cool to ambient temperature. The reaction mixture was evaporated to near dryness. Poured onto ice/water with stirring. A solid precipitate was collected by filtration. This was dried overnight under vacuum to afford the product (0.928 g, 75%). 1H NMR (400 MHz, DMSO) δ 8.02-7.96 (1H, t), 8.26 (1H, d), 8.28 (1H, s), 9.05 (2H, d). m/z M+=289; GCMS tR=13.82 min.

Workup

  1. temperatureto cool to ambient temperature
  2. customThe reaction mixture was evaporated
  3. additionPoured onto ice/water
  4. stirringwith stirring
  5. filtrationA solid precipitate was collected by filtration
  6. customThis was dried overnight under vacuum

Sources & evidence

ORD record
ord-2db84b18f15849ddb0b06c1c2f7da6bc
Source dataset
uspto-grants-2011_12
Patent number
US08071608B2

Reaction notes

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