Sodium Fluoride → {5-Amino-1-[2-(trityloxy)ethyl]pyrazol-4-yl}methylamine

HRID 349533Notes

Reaction equation

HRID 349533 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[NH2:7][C:8]1[N:12]([CH2:13][CH2:14][O: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)[N:11]=[CH:10][C:9]=1[C:35]#[N:36].[F-].[Na+].ClCCl>O1CCCC1.O>[NH2:7][C:8]1[N:12]([CH2:13][CH2:14][O:15][C:16]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)([C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[N:11]=[CH:10][C:9]=1[CH2:35][NH2:36]

Participants

7

Reactant 4

HCID 5235Sodium FluorideHCID 6344DichloromethaneHCID 179620185-Amino-1-[2-(trityloxy)ethyl]pyrazole-4-carbonitrileHCID 21226445Aluminium lithium hydride

Product 1

HCID 17961999{5-Amino-1-[2-(trityloxy)ethyl]pyrazol-4-yl}methylamineYield 77.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of lithium aluminum hydride (4.89 g, 129 mmol) in tetrahydrofuran (318 ml) was added 5-amino-1-[2-(trityloxy)ethyl]pyrazole-4-carbonitrile (25.4 g, 64.4 mmol) at room temperature. The mixture was stirred under reflux for 12 hours. After cooling on an ice bath, sodium fluoride (25.4 g), tetrahydrofuran (100 ml), dichloromethane (200 ml) and water (10 ml) were added to the reaction mixture. The insoluble materials were removed by filtration. The filtrate was concentrated in vacuo to give {5-amino-1-[2-(trityloxy)ethyl]pyrazol-4-yl}methylamine (19.8 g) as a solid.

Workup

  1. temperatureunder reflux for 12 hours
  2. temperatureAfter cooling on an ice bath
  3. customThe insoluble materials were removed by filtration
  4. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-a7c864b5051d44e0947db4cbc9ed8918
Source dataset
uspto-grants-2007_02
Patent number
US07179801B2

Reaction notes

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