Water → N-(6-(5-amino-7-(2-furyl)-3H-[1,2,3]triazolo[4,5-d]pyrimidin-3-ylmethyl)-2-pyridylmethyl)-N-methyltrifluoroacetamide

HRID 733010Notes

Reaction equation

HRID 733010 reaction equation
[CH3:1][NH:2][C:3](=[O:8])[C:4]([F:7])([F:6])[F:5].[H-].[Na+].Br[CH2:12][C:13]1[N:18]=[C:17]([CH2:19][N:20]2[C:24]3[N:25]=[C:26]([NH2:34])[N:27]=[C:28]([C:29]4[O:30][CH:31]=[CH:32][CH:33]=4)[C:23]=3[N:22]=[N:21]2)[CH:16]=[CH:15][CH:14]=1.O>CN(C=O)C>[NH2:34][C:26]1[N:27]=[C:28]([C:29]2[O:30][CH:31]=[CH:32][CH:33]=2)[C:23]2[N:22]=[N:21][N:20]([CH2:19][C:17]3[N:18]=[C:13]([CH2:12][N:2]([CH3:1])[C:3](=[O:8])[C:4]([F:7])([F:6])[F:5])[CH:14]=[CH:15][CH:16]=3)[C:24]=2[N:25]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 69948Acetamide, 2,2,2-trifluoro-N-methyl-HCID 218746303-(6-bromomethyl-2-pyridylmethyl)-7-(2-furyl)-3H-[1,2,3]triazolo[4,5-d]pyrimidine-5-amine

Product 1

HCID 86611049N-(6-(5-amino-7-(2-furyl)-3H-[1,2,3]triazolo[4,5-d]pyrimidin-3-ylmethyl)-2-pyridylmethyl)-N-methyltrifluoroacetamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of N-methyl-2,2,2-trifluoroacetamide (197 mg, 1.55 mmol) in DMF (5 mL) at 0° C. was treated with sodium hydride (60% dispersion in mineral oil; 62 mg, 1.55 mmol), stirred for 15 min, treated with 3-(6-bromomethyl-2-pyridylmethyl)-7-(2-furyl)-3H-[1,2,3]triazolo[4,5-d]pyrimidine-5-amine (120 mg, 0.310 mmol), stirred at 50° C. for 1 h, cooled to room temperature, poured into water (20 mL), extracted with EtOAc (3×10 mL) and the combined organic phase dried (MgSO4) and concentrated in vacuo to give N-(6-(5-amino-7-(2-furyl)-3H-[1,2,3]triazolo[4,5-d]pyrimidin-3-ylmethyl)-2-pyridylmethyl)-N-methyltrifluoroacetamide. A solution of this product in MeOH (20 mL) was treated with a solution of sodium (71 mg, 3.10 mmol) in MeOH (10 mL), stirred for 16 h, concentrated in vacuo, treated with EtOAc (20 mL), filtered through Celite and concentrated in vacuo. The resulting solid was suspended in MeOH (2 mL), treated with HCl (4-M in dioxane, 1.0 mL), stirred for 10 min, concentrated in vacuo and triturated with Et2O to give the title compound (80 mg, 58%) as a yellow solid.

Workup

  1. stirringstirred at 50° C. for 1 h
  2. extractionextracted with EtOAc (3×10 mL)
  3. dry with materialthe combined organic phase dried (MgSO4)
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a60e762aa1184a23a6ed1c6c7fae70af
Source dataset
uspto-grants-2009_09
Patent number
US07589097B2

Reaction notes

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