Water → HCID 21874759, compound

HRID 733014Notes

Reaction equation

HRID 733014 reaction equation
[NH2:1][C:2]1[N:3]=[C:4]([C:25]2[O:26][CH:27]=[CH:28][CH:29]=2)[C:5]2[N:10]=[N:9][N:8]([CH2:11][C:12]3[CH:17]=[CH:16][C:15]([NH:18][C:19](=O)[O:20]CC)=[C:14]([CH3:24])[CH:13]=3)[C:6]=2[N:7]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3].[OH-].[Na+].O>C1COCC1>[NH2:1][C:2]1[N:3]=[C:4]([C:25]2[O:26][CH:27]=[CH:28][CH:29]=2)[C:5]2[N:10]=[N:9][N:8]([CH2:11][C:12]3[CH:17]=[CH:16][C:15]([NH:18][CH:19]=[O:20])=[C:14]([CH3:24])[CH:13]=3)[C:6]=2[N:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 10135175HCID 10135175, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 21874759HCID 21874759, compoundYield 7.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of ethyl 4-((5-amino-7-(2-furyl)-3H-[1,2,3]triazolo[4,5-d]pyrimidine-3-yl)methyl)-2-methylphenylcarbamate (318 mg, 0.81 mmol) and LiAlH4 (62 mg, 1.62 mmol) in dry THF (30 mL) was refluxed overnight, cooled to room temperature, treated with 13% aqueous NaOH solution (0.1 mL) then water (0.3 mL), stirred for 30 min, filtered through Celite and concentrated in vacuo. The resulting solid was triturated with THF and filtered to give the title compound (20 mg, 7%) as a yellow solid.

Workup

  1. temperaturewas refluxed overnight
  2. filtrationfiltered through Celite
  3. concentrationconcentrated in vacuo
  4. customThe resulting solid was triturated with THF
  5. filtrationfiltered

Sources & evidence

ORD record
ord-2fe827aec1e74c818e3694ec75c1eb0c
Source dataset
uspto-grants-2009_09
Patent number
US07589097B2

Reaction notes

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