Phosphorus oxychloride → HCID 57438646, compound

HRID 1098133Notes

Reaction equation

HRID 1098133 reaction equation
P(Cl)(Cl)([Cl:3])=O.[CH3:6][C:7]1[CH:8]=[N:9][CH:10]=[CH:11][C:12]=1[N:13]1[C:21]2[NH:20][CH:19]=[N:18][C:17](=O)[C:16]=2[CH:15]=[N:14]1>>[Cl:3][C:17]1[N:18]=[CH:19][N:20]=[C:21]2[N:13]([C:12]3[CH:11]=[CH:10][N:9]=[CH:8][C:7]=3[CH3:6])[N:14]=[CH:15][C:16]=12

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178430468HCID 178430468, compound

Product 1

HCID 57438646HCID 57438646, compoundYield 72%

Conditions

Temperature
100 °C

Procedure

Phosphoryl trichloride (7.59 mL, 79.2 mmol) was added to 1-(3-methylpyridin-4-yl)-7H-pyrazolo[4,5-e]pyrimidin-4-one (Intermediate M2) (900 mg, 3.96 mmol) and the resulting suspension was stirred at 100° C. for 24 hours during which a solution formed. This was evaporated, triturated with ether (3×10 mL) and dried in vacuo. The resulting solid was suspended in DCM (50 mL) and stirred with 10 g of polymer supported carbonate for 2 hours. The mixture was filtered and evaporated to afford 4-chloro-1-(3-methylpyridin-4-yl)pyrazolo[5,4-d]pyrimidine (700 mg, 72%). 1H NMR (400 MHz, DMSO-d6) δ 2.25 (3H, s), 7.62 (1H, d), 8.64 (1H, d), 8.74 (1H, s), 8.83 (1H, s), 8.94 (1H, s); m/z (ESI+) (M+H)+=246; HPLC tR=1.22 min.

Workup

  1. customformed
  2. customThis was evaporated
  3. customtriturated with ether (3×10 mL)
  4. customdried in vacuo
  5. stirringstirred with 10 g of polymer
  6. customfor 2 hours
  7. filtrationThe mixture was filtered
  8. customevaporated

Sources & evidence

ORD record
ord-3259097216774ff99c8ede0b79bfec3b
Source dataset
uspto-grants-2012_03
Patent number
US08143263B2

Reaction notes

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