Phosphorus oxychloride → HCID 57438658, compound

HRID 1098180Notes

Reaction equation

HRID 1098180 reaction equation
P(Cl)(Cl)([Cl:3])=O.[Cl:6][C:7]1[C:8]([CH3:23])=[C:9]([N:13]2[C:17]3=[N:18][CH:19]=[N:20][C:21](O)=[C:16]3[CH:15]=[N:14]2)[CH:10]=[CH:11][CH:12]=1>>[Cl:3][C:21]1[N:20]=[CH:19][N:18]=[C:17]2[N:13]([C:9]3[CH:10]=[CH:11][CH:12]=[C:7]([Cl:6])[C:8]=3[CH3:23])[N:14]=[CH:15][C:16]=12

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178427905HCID 178427905, compound

Product 1

HCID 57438658HCID 57438658, compoundYield 87.2%

Conditions

Temperature
100 °C

Procedure

Phosphoryl trichloride (16.09 mL, 172.63 mmol) was added in one portion to 1-(3-chloro-2-methylphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-ol (Intermediate AE6) (3.0 g, 11.51 mmol) and the resulting suspension was heated to 100° C. to give a solution and stirred for 4 hours. Evaporated, the residue poured into ice/water and stirred for 30 minutes. The solids were filtered, washed with water (4×20 mL), dissolved in ethyl acetate (100 mL), dried (MgSO4), filtered and evaporated to afford the product (2.8 g) which was used without further purification. 1H NMR (400 MHz, DMSO) δ 2.06 (3H, s), 7.41-7.54 (2H, m), 7.71-7.73 (1H, m), 8.79 (1H, s), 8.89 (1H, s); m/z (ESI+) (M+H)+=279; HPLC tR=2.59 min.

Workup

  1. customto give a solution
  2. customEvaporated
  3. additionthe residue poured into ice/water
  4. stirringstirred for 30 minutes
  5. filtrationThe solids were filtered
  6. washwashed with water (4×20 mL)
  7. dissolutiondissolved in ethyl acetate (100 mL)
  8. dry with materialdried (MgSO4)
  9. filtrationfiltered
  10. customevaporated

Sources & evidence

ORD record
ord-8887d1b99c8b47bbb0b9a042e041ea1f
Source dataset
uspto-grants-2012_03
Patent number
US08143263B2

Reaction notes

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