Methylhydrazine → (S)-N2-(3-bromopyrazolo[1,5-a]pyrimidin-5-yl)-3-methylbutane-1,2-diamine

HRID 539026Notes

Reaction equation

HRID 539026 reaction equation
[Br:1][C:2]1[CH:3]=[N:4][N:5]2[CH:10]=[CH:9][C:8]([NH:11][C@@H:12]([CH:25]([CH3:27])[CH3:26])[CH2:13][N:14]3C(=O)C4C(=CC=CC=4)C3=O)=[N:7][C:6]=12.CNN>CO>[Br:1][C:2]1[CH:3]=[N:4][N:5]2[CH:10]=[CH:9][C:8]([NH:11][C@@H:12]([CH:25]([CH3:27])[CH3:26])[CH2:13][NH2:14])=[N:7][C:6]=12

Participants

4

Reactant 2

HCID 6061MethylhydrazineHCID 67033014(S)-2-(2-(3-bromopyrazolo[1,5-a]pyrimidin-5-ylamino)-3-methylbutyl)isoindoline-1,3-dione

Product 1

HCID 67035046(S)-N2-(3-bromopyrazolo[1,5-a]pyrimidin-5-yl)-3-methylbutane-1,2-diamineYield 83%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of (S)-2-(2-(3-bromopyrazolo[1,5-a]pyrimidin-5-ylamino)-3-methylbutyl)isoindoline-1,3-dione (3.8 g, 8.9 mmol) in methanol was added methylhydrazine (4.1 g, 89 mmol) and the reaction stirred overnight at ambient temperature. The reaction was concentrated and the residue was purified by chromatography, eluting with 10% MeOH/dichloromethane to 5% MeOH solution containing 7M ammonia/dichloromethane to yield (S)—N2-(3-bromopyrazolo[1,5-a]pyrimidin-5-yl)-3-methylbutane-1,2-diamine (2.2 g, 83%).

Workup

  1. concentrationThe reaction was concentrated
  2. customthe residue was purified by chromatography
  3. washeluting with 10% MeOH/dichloromethane to 5% MeOH solution
  4. additioncontaining 7M ammonia/dichloromethane

Sources & evidence

ORD record
ord-f10f3f2632c14d778d5ab35a1a571fcb
Source dataset
uspto-grants-2014_10
Patent number
US08865726B2

Reaction notes

Loading…