Phosphorus oxychloride → HCID 90408501, compound

HRID 1521677Notes

Reaction equation

HRID 1521677 reaction equation
[Br:1][C:2]1[CH:20]=[CH:19][C:5]([CH2:6][N:7]2[CH:15]=[C:14]3[C:9]([NH:10][C:11](=O)[N:12]([CH3:17])[C:13]3=[O:16])=[N:8]2)=[CH:4][CH:3]=1.O=P(Cl)(Cl)[Cl:23]>>[Cl:23][C:11]1[N:12]([CH3:17])[C:13](=[O:16])[C:14]2[C:9](=[N:8][N:7]([CH2:6][C:5]3[CH:19]=[CH:20][C:2]([Br:1])=[CH:3][CH:4]=3)[CH:15]=2)[N:10]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 136614171HCID 136614171, compound

Product 1

HCID 90408501HCID 90408501, compoundYield 94%

Conditions

Temperature
0 °C

Procedure

2-(4-Bromobenzyl)-5-methyl-2H-pyrazolo[3,4-d]pyrimidine-4,6(5H,7H)-dione (159 g, 475 mmol) is suspended in POCl3 (300 mL), and then slowly heated to reflux. After the mixture is refluxed for 60 h, POCl3 is removed under reduced pressure. The obtained residue is dissolved in methylene chloride (5 L), cooled to 0° C., and then adjusted to pH 8-9 with saturated sodium bicarbonate. After filtration, the obtained solids are washed with water twice, and then dried under vacuum to give 157 g of product (yield: 94%). MS (ESI) m/z 353.0 [M+H]+.

Workup

  1. temperatureslowly heated to reflux
  2. temperatureAfter the mixture is refluxed for 60 h
  3. customPOCl3 is removed under reduced pressure
  4. dissolutionThe obtained residue is dissolved in methylene chloride (5 L)
  5. filtrationAfter filtration
  6. washthe obtained solids are washed with water twice
  7. customdried under vacuum

Sources & evidence

ORD record
ord-6b53c2bdb25f480bbb30ffeafdaac085
Source dataset
uspto-grants-2015_07
Patent number
US09073936B2

Reaction notes

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