HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Reaction

Ethanol → tert-butyl 2-(4-amino-3-(4,5-dihydro-1H-imidazol-2-yl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)acetate

HRID 1798742
Notes
Print preview

Reaction equation

HRID 1798742 reaction equation
[C:1]([O:5][C:6](=[O:20])[CH2:7][N:8]1[C:12]2=[N:13][CH:14]=[N:15][C:16]([NH2:17])=[C:11]2[C:10]([C:18]#[N:19])=[N:9]1)([CH3:4])([CH3:3])[CH3:2].CCO.[CH2:24](N)[CH2:25][NH2:26]>C(O)(=O)C>[NH2:17][C:16]1[N:15]=[CH:14][N:13]=[C:12]2[N:8]([CH2:7][C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:20])[N:9]=[C:10]([C:18]3[NH:26][CH2:25][CH2:24][N:19]=3)[C:11]=12
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 702EthanolHCID 3301EthylenediamineHCID 59242680(4-Amino-3-cyano-pyrazolo[3,4-d]pyrimidin-1-yl)-acetic acid tert-butyl ester

Product 1

HCID 59242681tert-butyl 2-(4-amino-3-(4,5-dihydro-1H-imidazol-2-yl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)acetateYield 90%

Reagents, catalysts & solvents 1

HCID 176Acetic Acid
Solvent

Procedure

To a mixture of (4-amino-3-cyano-pyrazolo[3,4-d]pyrimidin-1-yl)-acetic acid tert-butyl ester (80 g, 0.291 mol) and EtOH (800 mL) in an ice water bath was added acetic acid (67 mL) and then ethylenediamine (195 mL). The resulting mixture was refluxed for 90 min, cooled to room temperature and filtered. The solid was suspended in water (1 L), filtered and dried in vacuo to give of tert-butyl 2-(4-amino-3-(4,5-dihydro-1H-imidazol-2-yl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)acetate (84.6 g, 90% yield). MS (ES) m/z 318.1 (M+H+).

Workup

  1. temperatureThe resulting mixture was refluxed for 90 min
  2. filtrationfiltered
  3. filtrationfiltered
  4. customdried in vacuo

Sources & evidence

ORD record
ord-226d8017485748548e10af502a235723
Source dataset
uspto-grants-2013_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08343975B2

Reaction notes

Loading…

On this pageParticipantsProcedureWorkupSources & evidenceReaction notes