Phosphorus oxychloride → HCID 178480563, compound

HRID 72692Notes

Reaction equation

HRID 72692 reaction equation
[CH3:1][N:2]1[C:7](=[O:8])[C:6]2[C:9]([NH:12][C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)=[N:10][NH:11][C:5]=2[NH:4][C:3]1=O.O=P(Cl)(Cl)[Cl:22]>>[Cl:22][C:3]1[N:2]([CH3:1])[C:7](=[O:8])[C:6]2[C:9]([NH:12][C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)=[N:10][NH:11][C:5]=2[N:4]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178481638HCID 178481638, compound

Product 1

HCID 178480563HCID 178480563, compoundYield 72%

Procedure

5-methyl-3-(phenylamino)-1H-pyrazolo[3,4-d]pyrimidine-4,6(5H,7H)-dione (4.3 g, 16.7 mmol) is refluxed in POCl3 (120 mL) for 2 days, and then POCl3 is removed under reduced pressure. The residue is suspended in 100 mL of water and carefully adjusted to pH=1˜2 with 7% NH4OH upon cooling. The mixture is then extracted with CH2Cl2 and MeOH (10:1, v/v) five times. The combined organic phase is washed with water, dried over Na2SO4, and then evaporated under reduced vacuum to give 3.3 g of crude product (Yield: 72%). MS (ESI) m/z 276.1 [M+H]+.

Workup

  1. customPOCl3 is removed under reduced pressure
  2. temperatureupon cooling
  3. extractionThe mixture is then extracted with CH2Cl2 and MeOH (10:1
  4. washThe combined organic phase is washed with water
  5. dry with materialdried over Na2SO4
  6. customevaporated under reduced vacuum

Sources & evidence

ORD record
ord-ee0d7c5d74ae4630b11b983fd43f298f
Source dataset
uspto-grants-2014_09
Patent number
US08829008B2

Reaction notes

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