Hydrazine hydrate (1:1) → N4-(6-aminohexahydrofuro[3,2-b]furan-3-yl)-5-chloro-N2-(1-methyl-1H-pyrazol-4-yl)pyrimidine-2,4-diamine

HRID 1053944Notes

Reaction equation

HRID 1053944 reaction equation
[Cl:1][C:2]1[C:3]([NH:15][CH:16]2[CH:20]3[O:21][CH2:22][CH:23]([N:24]4C(=O)C5C(=CC=CC=5)C4=O)[CH:19]3[O:18][CH2:17]2)=[N:4][C:5]([NH:8][C:9]2[CH:10]=[N:11][N:12]([CH3:14])[CH:13]=2)=[N:6][CH:7]=1.O.NN>CCO>[NH2:24][CH:23]1[CH:19]2[O:18][CH2:17][CH:16]([NH:15][C:3]3[C:2]([Cl:1])=[CH:7][N:6]=[C:5]([NH:8][C:9]4[CH:10]=[N:11][N:12]([CH3:14])[CH:13]=4)[N:4]=3)[CH:20]2[O:21][CH2:22]1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 1183879602-(6-((5-chloro-2-((l-methyl-1H-pyrazol-4-yl)amino)pyrimidin-4-yl)amino)hexahydrofuro[3,2-b]furan-3-yl)isoindoline-1,3-dione

Product 1

HCID 118409773N4-(6-aminohexahydrofuro[3,2-b]furan-3-yl)-5-chloro-N2-(1-methyl-1H-pyrazol-4-yl)pyrimidine-2,4-diamineYield 63.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 2-(6-((5-chloro-2-((l-methyl-1H-pyrazol-4-yl)amino)pyrimidin-4-yl)amino)hexahydrofuro[3,2-b]furan-3-yl)isoindoline-1,3-dione (140.0 mg, 0.29 mmol) in EtOH (5 mL) was added hydrazine hydrate (198.6 mg, 2.94 mmol). The mixture was stirred at room temperature for 4 h. The mixture was concentrated in vacuo, the residue was purified with a silica gel column chromatography ((7M NH3 in MeOH)/DCM (v/v)=1/20) to give the target product as a white solid (65.0 mg, 63.6%).

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. customthe residue was purified with a silica gel column chromatography ((7M NH3 in MeOH)/DCM (v/v)=1/20)

Sources & evidence

ORD record
ord-1fd5423a5f124966bc2964ff6854d10c
Source dataset
uspto-grants-2016_07
Patent number
US09394281B2

Reaction notes

Loading…