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Water → 4-Aminomethyl-1-propyl-5-tritylaminopyrazole

HRID 349545
Notes
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Reaction equation

HRID 349545 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH2:7]([N:10]1[C:14]([NH:15][C:16]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[C:13]([C:35]#[N:36])[CH:12]=[N:11]1)[CH2:8][CH3:9].[F-].[Na+].O>O1CCCC1>[NH2:36][CH2:35][C:13]1[CH:12]=[N:11][N:10]([CH2:7][CH2:8][CH3:9])[C:14]=1[NH:15][C:16]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)([C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 962WaterHCID 5235Sodium FluorideHCID 17961964HCID 17961964, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 179619914-Aminomethyl-1-propyl-5-tritylaminopyrazoleYield 81.1%

Reagents, catalysts & solvents 1

HCID 8028
Tetrahydrofuran
Solvent

Procedure

To a suspension of lithium aluminum hydride (8.94 g) in tetrahydrofuran (600 ml) was added 1-propyl-5-tritylamino-1H-pyrazole-4-carbonitrile (37 g) at room temperature. The mixture was refluxed for 7 days. After cooling on an ice bath, sodium fluoride (40 g) and water (17 ml) were added to the reaction mixture. The insoluble materials were removed by filtration. To the filtrate was added ethyl formate, and the mixture was refluxed for 24 hours. After evaporation of the solvent in vacuo, the residue was triturated with diisopropyl ether and dried in vacuo to give 4-aminomethyl-1-propyl-5-tritylaminopyrazole (30.3 g).

Workup

  1. temperatureThe mixture was refluxed for 7 days
  2. temperatureAfter cooling on an ice bath
  3. customThe insoluble materials were removed by filtration
  4. additionTo the filtrate was added ethyl formate
  5. temperaturethe mixture was refluxed for 24 hours
  6. customAfter evaporation of the solvent in vacuo
  7. customthe residue was triturated with diisopropyl ether
  8. customdried in vacuo

Sources & evidence

ORD record
ord-2dde7729a76648eba2e1253a4f79fc1d
Source dataset
uspto-grants-2007_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07179801B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes