Water → 3-(6-Cyanomethyl-2-Pyridylmethyl)-7-(2-Furyl)-3H-[1,2,3]Triazolo[4,5-D]Pyrimidine-5-Amine

HRID 733008Notes

Reaction equation

HRID 733008 reaction equation
Br[CH2:2][C:3]1[N:8]=[C:7]([CH2:9][N:10]2[C:14]3[N:15]=[C:16]([NH2:24])[N:17]=[C:18]([C:19]4[O:20][CH:21]=[CH:22][CH:23]=4)[C:13]=3[N:12]=[N:11]2)[CH:6]=[CH:5][CH:4]=1.[C-:25]#[N:26].[Na+].O>CN(C=O)C>[C:25]([CH2:2][C:3]1[N:8]=[C:7]([CH2:9][N:10]2[C:14]3[N:15]=[C:16]([NH2:24])[N:17]=[C:18]([C:19]4[O:20][CH:21]=[CH:22][CH:23]=4)[C:13]=3[N:12]=[N:11]2)[CH:6]=[CH:5][CH:4]=1)#[N:26]

Participants

5

Reactant 3

HCID 962WaterHCID 8929Sodium CyanideHCID 218746303-(6-bromomethyl-2-pyridylmethyl)-7-(2-furyl)-3H-[1,2,3]triazolo[4,5-d]pyrimidine-5-amine

Product 1

HCID 218745493-(6-Cyanomethyl-2-Pyridylmethyl)-7-(2-Furyl)-3H-[1,2,3]Triazolo[4,5-D]Pyrimidine-5-AmineYield 29.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 3-(6-bromomethyl-2-pyridylmethyl)-7-(2-furyl)-3H-[1,2,3]triazolo[4,5-d]pyrimidine-5-amine (200 mg, 0.517 mmol) and sodium cyanide (51 mg, 1.03 mmol) in DMF (5 mL) was stirred at 60° C. for 16 h, poured into water (40 mL), extracted with EtOAc (3×8 mL), the combined organic phase dried (MgSO4), concentrated in vacuo and purified by chromatography [SiO2;isohexane:EtOAc (1:1)] to give title compound (50 mg, 26%) as a yellow solid.

Workup

  1. extractionextracted with EtOAc (3×8 mL)
  2. dry with materialthe combined organic phase dried (MgSO4)
  3. concentrationconcentrated in vacuo
  4. custompurified by chromatography [SiO2;isohexane:EtOAc (1:1)]

Sources & evidence

ORD record
ord-3ccfbc0c18c14568a0343dcd7abd275d
Source dataset
uspto-grants-2009_09
Patent number
US07589097B2

Reaction notes

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