Glycol monoethyl ether → 3-(6-Ethoxyethoxymethylpyridin-2-ylmethyl)-7-(5-methyl-2-furyl)-3H-[1,2,3]triazolo[4,5-d]pyrimidin-5-ylamine

HRID 876989Notes

Reaction equation

HRID 876989 reaction equation
[CH2:1]([O:3][CH2:4][CH2:5][OH:6])[CH3:2].[H-].[Na+].Br[CH2:10][C:11]1[N:16]=[C:15]([CH2:17][N:18]2[C:22]3[N:23]=[C:24]([NH2:33])[N:25]=[C:26]([C:27]4[O:28][C:29]([CH3:32])=[CH:30][CH:31]=4)[C:21]=3[N:20]=[N:19]2)[CH:14]=[CH:13][CH:12]=1>C1COCC1>[CH2:1]([O:3][CH2:4][CH2:5][O:6][CH2:10][C:11]1[N:16]=[C:15]([CH2:17][N:18]2[C:22]3[N:23]=[C:24]([NH2:33])[N:25]=[C:26]([C:27]4[O:28][C:29]([CH3:32])=[CH:30][CH:31]=4)[C:21]=3[N:20]=[N:19]2)[CH:14]=[CH:13][CH:12]=1)[CH3:2]

Participants

5

Reactant 3

HCID 8076Glycol monoethyl etherHCID 24758Sodium hydrideHCID 667183513-(6-Bromomethylpyridin-2-ylmethyl)-7-(5-methyl-2-furyl)-3H-[1,2,3]triazolo[4,5-d]pyrimidin-5-ylamine

Product 1

HCID 445553143-(6-Ethoxyethoxymethylpyridin-2-ylmethyl)-7-(5-methyl-2-furyl)-3H-[1,2,3]triazolo[4,5-d]pyrimidin-5-ylamineYield 33.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 2-ethoxyethanol (242 μl, 2.5 mmol) in anhydrous THF (15 mL) was cooled to 0° C. and treated with NaH (100 mg, 2.5 mmol). The reaction was stirred at 0° C. for 10 mins, then treated with 3-(6-bromomethylpyridin-2-ylmethyl)-7-(5-methyl-2-furyl)-3H-[1,2,3]triazolo[4,5-d]pyrimidin-5-ylamine (100 mg, 0.25 mmol), stirred at room temperature for 30 mins. The reaction was quenched with aqueous NH4Cl and extracted with EtOAc. The combined organic phases were dried (MgSO4) and concentrated in vacuo. The resulting solid was suspended in MeOH (10 mL) and treated with 4M HCl in dioxane (2 mL), the reaction mixture was then diluted with diethyl ether (40 mL) and the resulting solid isolated by filtration to give the product (34 mg, 31%) as a yellow solid.

Workup

  1. stirringstirred at room temperature for 30 mins
  2. customThe reaction was quenched with aqueous NH4Cl
  3. extractionextracted with EtOAc
  4. dry with materialThe combined organic phases were dried (MgSO4)
  5. concentrationconcentrated in vacuo
  6. additiontreated with 4M HCl in dioxane (2 mL)
  7. additionthe reaction mixture was then diluted with diethyl ether (40 mL)
  8. customthe resulting solid isolated by filtration

Sources & evidence

ORD record
ord-aa5c602dc04244919e123f4af713c59f
Source dataset
uspto-grants-2015_03
Patent number
US08987279B2

Reaction notes

Loading…