Nitric Acid → HCID 178437876, compound

HRID 1600812Notes

Reaction equation

HRID 1600812 reaction equation
[N+:1]([O-:4])(O)=[O:2].[CH:5]1([N:10]2[C:14]3=[N:15][C:16]([CH2:20][C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=4)=[N:17][C:18](=[O:19])[C:13]3=[C:12]([CH2:27][CH3:28])[NH:11]2)[CH2:9][CH2:8][CH2:7][CH2:6]1>>[CH:5]1([N:10]2[C:14]3=[N:15][C:16]([CH2:20][C:21]4[CH:22]=[CH:23][C:24]([N+:1]([O-:4])=[O:2])=[CH:25][CH:26]=4)=[N:17][C:18](=[O:19])[C:13]3=[C:12]([CH2:27][CH3:28])[NH:11]2)[CH2:6][CH2:7][CH2:8][CH2:9]1

Participants

3

Reactant 2

HCID 944Nitric AcidHCID 178437867HCID 178437867, compound

Product 1

HCID 178437876HCID 178437876, compound

Procedure

To 90% HNO3 (95 mL) at -10 to -15° C. was added 1-cyclopentyl-3-ethyl-6-(phenylmethyl)pyrazolo[3,4-d]pyrimidin-4-one (9.62 g, 30 mmol) . The reaction mixture was stirred as such for 1.5 hours, and then was poured into ice water. A precipitate formed which was collected by filtration, recrystallized from ethyl acetate and dried at 100° C. and 0.2 mm Hg to afford 2.31 g of 1-cyclopentyl-3-ethyl-6-(4-nitrophenylmethyl)pyrazolo[3,4-d]pyrimidin-4-one, m.p. 221-223° C. [labelled as Example 25 (a)]. The mother liquors were combined and concentrated in vacuo to afford a mixture of 1-cyclopentyl-3-ethyl-6-(2-nitrophenylmethyl)pyrazolo [3,4-d]pyrimidin-4-one and 1-cyclopentyl-3-ethyl-6-(3-nitrophenyl methyl)pyrazolo[3,4-d]pyrimidin-4-one [ labelled as Example 25 (b)].

Workup

  1. customA precipitate formed which
  2. filtrationwas collected by filtration
  3. customrecrystallized from ethyl acetate
  4. customdried at 100° C.

Sources & evidence

ORD record
ord-064c4e895ccd42ac8cc7f906753e6144
Source dataset
uspto-grants-1999_11
Patent number
US05977118

Reaction notes

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