Phosphorus oxychloride → HCID 57504627, compound

HRID 1098150Notes

Reaction equation

HRID 1098150 reaction equation
P(Cl)(Cl)([Cl:3])=O.[CH3:6][C:7]1[CH:12]=[CH:11][N:10]=[CH:9][C:8]=1[N:13]1[C:17]2=[N:18][CH:19]=[N:20][C:21](O)=[C:16]2[CH:15]=[N:14]1>>[Cl:3][C:21]1[N:20]=[CH:19][N:18]=[C:17]2[N:13]([C:8]3[CH:9]=[N:10][CH:11]=[CH:12][C:7]=3[CH3:6])[N:14]=[CH:15][C:16]=12

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178428398HCID 178428398, compound

Product 1

HCID 57504627HCID 57504627, compound

Conditions

Temperature
100 °C

Procedure

Phosphorus oxychloride (5.10 ml, 54.75 mmol) was added to 1-(4-methylpyridin-3-yl)-1H-pyrazolo[3,4-d]pyrimidin-4-ol (0.622 g, 2.74 mmol). The resulting solution was stirred at 100° C. for 2 hours. The reaction mixture was evaporated. Toluene was added to the residue and the reaction mixture was concentrated. This was repeated to remove excess POCl3. The residue was dissolved in DMF (15 mL) and MP carbonate was added (˜3 g) and allowed to stir overnight. The DMF was evaporated in vacuo to afford crude product which was used without further purification. 1H NMR (400 MHz, DMSO) δ 2.1 (3H, s), 7.60 (1H, d), 8.65 (1H, d), 8.68 (1H, s), 8.82 (1H, s), 8.91 (1H, s); m/z (ES+) (M+H)+=246; HPLC tR=1.69 min.

Workup

  1. customThe reaction mixture was evaporated
  2. additionToluene was added to the residue
  3. concentrationthe reaction mixture was concentrated
  4. customto remove excess POCl3
  5. dissolutionThe residue was dissolved in DMF (15 mL)
  6. additionMP carbonate was added (˜3 g)
  7. stirringto stir overnight
  8. customThe DMF was evaporated in vacuo
  9. customto afford crude product which
  10. customwas used without further purification

Sources & evidence

ORD record
ord-21493b3a92674f65bf91fb144faef8e8
Source dataset
uspto-grants-2012_03
Patent number
US08143263B2

Reaction notes

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