Dimethylformamide → 7-(4-methoxybenzyl)-5-methyl-2H-pyrazolo[3,4-d]pyrimidine-4,6(5H,7H)-dione

HRID 81410

Reaction equation

HRID 81410 reaction equation
[NH:1]([C:3]1[N:8]([CH2:9][C:10]2[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][CH:11]=2)[C:7](=[O:18])[N:6]([CH3:19])[C:5](=[O:20])[CH:4]=1)[NH2:2].O=P(Cl)(Cl)Cl.[CH3:26]N(C=O)C>>[CH3:17][O:16][C:13]1[CH:14]=[CH:15][C:10]([CH2:9][N:8]2[C:3]3[NH:1][N:2]=[CH:26][C:4]=3[C:5](=[O:20])[N:6]([CH3:19])[C:7]2=[O:18])=[CH:11][CH:12]=1

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 24813Phosphorus oxychlorideHCID 667954896-hydrazinyl-1-(4-methoxybenzyl)-3-methylpyrimidine-2,4(1H,3H)-dione

Product 1

HCID 685009507-(4-methoxybenzyl)-5-methyl-2H-pyrazolo[3,4-d]pyrimidine-4,6(5H,7H)-dioneYield 90%

Procedure

To a solution of 6-hydrazinyl-1-(4-methoxybenzyl)-3-methylpyrimidine-2,4(1H,3H)-dione (4.0 g, 14.5 mmol) in anhydrous DMF (200 mL) is added POCl3 (16 mL) dropwise with IPA-dry ice bath cooling. After the completion of the addition, the mixture is allowed to warm up to room temperature and stirred at r.t. overnight. DMF is removed under reduced pressure, and the residue is treated with cold water very carefully. The generated precipitate is filtered, washed with water to give pure product as white solids (3.74 g, yield: 90%). MS (ESI) m/z 287.1 [M+H]+

Workup

  1. temperaturecooling
  2. additionAfter the completion of the addition
  3. customDMF is removed under reduced pressure
  4. additionthe residue is treated with cold water very carefully
  5. filtrationThe generated precipitate is filtered
  6. washwashed with water

Sources & evidence

ORD record
ord-2e0d4ffbf76745588d221a311ed2a9b4
Source dataset
uspto-grants-2014_09
Patent number
US08846693B2

Linked notes

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