Sodium borohydride → 1-Ethyl-3-(5-hydroxymethyl-7-pyridin-3-yl-[1,2,4]triazolo[1,5-a]pyridin-2-yl)-urea

HRID 2112958Notes

Reaction equation

HRID 2112958 reaction equation
C([O:3][C:4]([C:6]1[N:11]2[N:12]=[C:13]([NH:15][C:16]([NH:18][CH2:19][CH3:20])=[O:17])[N:14]=[C:10]2[CH:9]=[C:8]([C:21]2[CH:22]=[N:23][CH:24]=[CH:25][CH:26]=2)[CH:7]=1)=O)C.[BH4-].[Na+]>C1COCC1.CO>[CH2:19]([NH:18][C:16]([NH:15][C:13]1[N:14]=[C:10]2[CH:9]=[C:8]([C:21]3[CH:22]=[N:23][CH:24]=[CH:25][CH:26]=3)[CH:7]=[C:6]([CH2:4][OH:3])[N:11]2[N:12]=1)=[O:17])[CH3:20]

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 576431092-(3-Ethyl-ureido)-7-pyridin-3-yl-[1,2,4]triazolo[1,5-a]pyridine-5-carboxylic acid ethyl ester

Product 1

HCID 688348081-Ethyl-3-(5-hydroxymethyl-7-pyridin-3-yl-[1,2,4]triazolo[1,5-a]pyridin-2-yl)-urea

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirring suspension of the product of Step 2, (0.88 g, 2.5 mmol) in THF (40 mL) and MeOH (5 mL) was added sodium borohydride (1.02 g, 27 mmol). After 1 h the reaction was quenched by the addition of ca. 50 mL water and stirred 1 h to allow formation of a precipitate. The solid was rinsed with water (3×10 mL) and dried in vacuo to give the alcohol, 1-ethyl-3-(5-hydroxymethyl-7-pyridin-3-yl-[1,2,4]triazolo[1,5-a]pyridin-2-yl)-urea as a solid.

Workup

  1. customAfter 1 h the reaction was quenched by the addition of ca. 50 mL water
  2. washThe solid was rinsed with water (3×10 mL)
  3. customdried in vacuo

Sources & evidence

ORD record
ord-5f61eb11734542ddbfd48fa79c145731
Source dataset
uspto-grants-2009_04
Patent number
US07524860B2

Reaction notes

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