Phosphorus oxychloride → HCID 86680708, compound

HRID 1500759Notes

Reaction equation

HRID 1500759 reaction equation
[N+:1]([C:4]1[C:5](O)=[N:6][C:7]([C:10]2[CH:11]=[N:12][N:13]3[CH:18]=[CH:17][N:16]=[CH:15][C:14]=23)=[N:8][CH:9]=1)([O-:3])=[O:2].P(Cl)(Cl)([Cl:22])=O>>[Cl:22][C:5]1[C:4]([N+:1]([O-:3])=[O:2])=[CH:9][N:8]=[C:7]([C:10]2[CH:11]=[N:12][N:13]3[CH:18]=[CH:17][N:16]=[CH:15][C:14]=23)[N:6]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178526803HCID 178526803, compound

Product 1

HCID 86680708HCID 86680708, compoundYield 86%

Conditions

Temperature
90 °C

Procedure

A suspension of 5-nitro-2-(pyrazolo[1,5-a]pyrazin-3-yl)pyrimidin-4-ol (Preparation 24d, 1.50 g, 5.8 mmol) in phosphoryl trichloride (12 mL) was stirred and heated to 90° C. in a sealed tube. After 2 hours, the mixture was concentrated in vacuo and the residue was azeotroped with toluene. The resultant solid was treated with saturated aqueous sodium hydrogen carbonate solution and, upon scratching, a solid formed which was filtered, washed with water (40 mL) and dried to give the title compound (1.38 g, 86%) as a yellow solid.

Workup

  1. concentrationthe mixture was concentrated in vacuo
  2. customthe residue was azeotroped with toluene
  3. additionThe resultant solid was treated with saturated aqueous sodium hydrogen carbonate solution
  4. customa solid formed which
  5. filtrationwas filtered
  6. washwashed with water (40 mL)
  7. customdried

Sources & evidence

ORD record
ord-2b5986abc31b483b89c611ed400a19e9
Source dataset
uspto-grants-2015_12
Patent number
US09206183B2

Reaction notes

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