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Diisopropyl Ether → 5-(5-amino-1-pentyn-1-yl)-N2-(3-fluorophenyl)-N4-propylpyrimidine-2,4-diamine

HRID 2284714
Notes
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Reaction equation

HRID 2284714 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([NH:8][C:9]2[N:14]=[C:13]([NH:15][CH2:16][CH2:17][CH3:18])[C:12]([C:19]#[C:20][CH2:21][CH2:22][CH2:23][N:24]3C(=O)C4C(=CC=CC=4)C3=O)=[CH:11][N:10]=2)[CH:5]=[CH:6][CH:7]=1.C(OC(C)C)(C)C>O1CCCC1.C(O)C.O.NN>[NH2:24][CH2:23][CH2:22][CH2:21][C:20]#[C:19][C:12]1[C:13]([NH:15][CH2:16][CH2:17][CH3:18])=[N:14][C:9]([NH:8][C:4]2[CH:5]=[CH:6][CH:7]=[C:2]([F:1])[CH:3]=2)=[N:10][CH:11]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 2

HCID 7914Diisopropyl EtherHCID 900522652-(5-(2-((3-Fluorophenyl)amino)-4-(propylamino)pyrimidin-5-yl)-4-pentyn-1-yl)isoindoline-1,3-dione

Product 1

HCID 900522675-(5-amino-1-pentyn-1-yl)-N2-(3-fluorophenyl)-N4-propylpyrimidine-2,4-diamineYield 61.2%

Reagents, catalysts & solvents 3

HCID 702EthanolSolvent2×
HCID 8028
Tetrahydrofuran
Solvent
HCID 24654Hydrazine hydrate (1:1)Solvent

Procedure

To a solution of 2-(5-(2-((3-fluorophenyl)amino)-4-(propylamino)pyrimidin-5-yl)-4-pentyn-1-yl)isoindoline-1,3-dione (F3, 2.51 g) in tetrahydrofuran (20 mL) and ethanol (10 mL), hydrazine monohydrate (5.1 mL) was added at room temperature, and the mixture was stirred for 10 minutes under reflux by heating. To the reaction mixture, ethanol (10 mL) was added, and the mixture was stirred at room temperature for 3 hours and 20 minutes. To the reaction mixture, diisopropyl ether was added, the insoluble matter was removed by filtration, and then water was added to the filtrate. The organic layer was separated, washed successively with saturated aqueous sodium hydrogencarbonate and saturated aqueous sodium chloride, and then dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure to obtain 5-(5-amino-1-pentyn-1-yl)-N2-(3-fluorophenyl)-N4-propylpyrimidine-2,4-diamine (F4, 1.10 g) as white solid.

Workup

  1. temperatureunder reflux
  2. temperatureby heating
  3. stirringthe mixture was stirred at room temperature for 3 hours and 20 minutes
  4. customthe insoluble matter was removed by filtration
  5. additionwater was added to the filtrate
  6. customThe organic layer was separated
  7. washwashed successively with saturated aqueous sodium hydrogencarbonate and saturated aqueous sodium chloride
  8. dry with materialdried over anhydrous magnesium sulfate
  9. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-3904b00c24db4d33a285b20201c6ad5b
Source dataset
uspto-grants-2015_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09145415B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes