tert-Butyl 3-amino-4,6-dihydropyrrolo[3,4-c]pyrazole-5(1H)-carboxylate → 1,4,5,6-Tetrahydropyrrolo[3,4-c]pyrazol-3-amine

HRID 241565Notes

Reaction equation

HRID 241565 reaction equation
[NH2:1][C:2]1[C:3]2[CH2:9][N:8](C(OC(C)(C)C)=O)[CH2:7][C:4]=2[NH:5][N:6]=1.C(O)(C(F)(F)F)=O.C(Cl)Cl>>[NH:5]1[C:4]2[CH2:7][NH:8][CH2:9][C:3]=2[C:2]([NH2:1])=[N:6]1

Participants

3

Reactant 2

HCID 11333571tert-Butyl 3-amino-4,6-dihydropyrrolo[3,4-c]pyrazole-5(1H)-carboxylateHCID 21863450Trifluoroacetic acid methylene chloride

Product 1

HCID 167845751,4,5,6-Tetrahydropyrrolo[3,4-c]pyrazol-3-amine

Procedure

tert-Butyl 3-amino-4,6-dihydropyrrolo[3,4-c]pyrazole-5(1H)-carboxylate (3670 mg, 16.36 mmol) was treated with TFA/CH2Cl2 (v/v=1/1) for 1 h. The reaction mixture was concentrated and the residue was treated with CH2Cl2/hexanes and then concentrated to give a solid. The product was passed through ion-exchange resin Strata X—C™ to give the title product (LC-MS: 125.05 (M+1)

Workup

  1. concentrationThe reaction mixture was concentrated
  2. additionthe residue was treated with CH2Cl2/hexanes
  3. concentrationconcentrated
  4. customto give a solid

Sources & evidence

ORD record
ord-9e6bd68a5bcb4f4c9408edfaa97042ae
Source dataset
uspto-grants-2014_02
Patent number
US08653059B2

Reaction notes

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