Nitric Acid → 5-[(2R)-2-(2,5-Difluorophenyl)-1-pyrrolidinyl]-3-nitropyrazolo[1,5-a]pyrimidine

HRID 2275326Notes

Reaction equation

HRID 2275326 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[C@H:9]1[CH2:13][CH2:12][CH2:11][N:10]1[C:14]1[CH:19]=[CH:18][N:17]2[N:20]=[CH:21][CH:22]=[C:16]2[N:15]=1.[N+:23]([O-])([OH:25])=[O:24]>C(O)(C(F)(F)F)=O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[C@H:9]1[CH2:13][CH2:12][CH2:11][N:10]1[C:14]1[CH:19]=[CH:18][N:17]2[N:20]=[CH:21][C:22]([N+:23]([O-:25])=[O:24])=[C:16]2[N:15]=1

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 67329909(R)-5-(2-(2,5-difluorophenyl)pyrrolidin-1-yl)pyrazolo[1,5-a]pyrimidine

Product 1

HCID 673298195-[(2R)-2-(2,5-Difluorophenyl)-1-pyrrolidinyl]-3-nitropyrazolo[1,5-a]pyrimidineYield 58%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

(R)-5-(2-(2,5-difluorophenyl)pyrrolidin-1-yl)pyrazolo[1,5-a]pyrimidine (3.3 g, 10.99 mmol), was dissolved in 25 mL TFA at ambient temperature to give a clear yellowish solution, then nitric acid (3.434 mL, 54.94 mmol) was added drop-wise to the solution with rapid stirring. After addition, the reaction mixture was stirred for another 15 minutes at ambient temperature, then quenched by pouring onto ice with rapid stirring. The resulting yellowish suspension was filtered, rinsed with water, then the solid was triturated with MeOH (50 mL, with brief sonication), and vacuum-filtered, giving the pure product as a fine off-white powder (2.2 g, 58% yield).

Workup

  1. customto give a clear yellowish solution
  2. additionAfter addition
  3. customquenched
  4. additionby pouring onto ice with rapid stirring
  5. filtrationThe resulting yellowish suspension was filtered
  6. washrinsed with water
  7. customthe solid was triturated with MeOH (50 mL, with brief sonication)
  8. filtrationvacuum-filtered

Sources & evidence

ORD record
ord-71055205699048d2bb5a58308bf4f4c1
Source dataset
uspto-grants-2015_09
Patent number
US09127013B2

Reaction notes

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