Sodium Hydroxide → 5-Amino-2-(2-furyl)-7-(4-(5-methylisoxazol-3-ylmethyl)piperazinyl)[1,2,4]triazolo[1,5-c]pyrimidine

HRID 1264876Notes

Reaction equation

HRID 1264876 reaction equation
[NH2:1][C:2]1[N:7]2[N:8]=[C:9]([C:11]3[O:12][CH:13]=[CH:14][CH:15]=3)[N:10]=[C:6]2[CH:5]=[C:4]([N:16]2[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]2)[N:3]=1.[CH3:22][C:23]1[O:27][N:26]=[C:25]([CH:28]=O)[CH:24]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[OH-].[Na+]>O.C(O)(=O)C.ClCCl>[NH2:1][C:2]1[N:7]2[N:8]=[C:9]([C:11]3[O:12][CH:13]=[CH:14][CH:15]=3)[N:10]=[C:6]2[CH:5]=[C:4]([N:16]2[CH2:17][CH2:18][N:19]([CH2:28][C:25]3[CH:24]=[C:23]([CH3:22])[O:27][N:26]=3)[CH2:20][CH2:21]2)[N:3]=1

Participants

8

Reactant 4

HCID 14798Sodium HydroxideHCID 27952225-Methyl-1,2-oxazole-3-carbaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 186136985-Amino-2-(2-furyl)-7-piperazinyl[1,2,4]triazolo[1,5-c]pyrimidine

Product 1

HCID 186136925-Amino-2-(2-furyl)-7-(4-(5-methylisoxazol-3-ylmethyl)piperazinyl)[1,2,4]triazolo[1,5-c]pyrimidineYield 11.1%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Into 15 mL of dichloromethane, 1.50 g (5.26 mmol) of Compound F and 934 mg (8.42 mmol) of 5-methylisoxazole-3-carboxaldehyde were dissolved, and the solution was cooled to 0° C. in an ice bath. Then, 1.5 mL of acetic acid and 1.78 g (8.42 mmol; 1.6 eq.) of sodium triacetoxyborohydride were added thereto, followed by stirring at room temperature overnight. After completion of the reaction, water was added to the reaction mixture, and a 1.0 mol/L aqueous sodium hydroxide solution was further added thereto to adjust the solution to be basic. Then, the mixture was extracted by adding chloroform, and the organic layer was washed with water and brine, and then dried over anhydrous magnesium sulfate. After evaporation of the solvent, the resulting residue was purified by silica gel column chromatography (2% methanol-chloroform) and then recrystallized from ethanol to obtain 222 mg of Compound 21 as white powder (yield: 11%).

Workup

  1. additionwas added to the reaction mixture
  2. extractionThen, the mixture was extracted
  3. additionby adding chloroform
  4. washthe organic layer was washed with water and brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customAfter evaporation of the solvent
  7. customthe resulting residue was purified by silica gel column chromatography (2% methanol-chloroform)
  8. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-8a4ace6c8dd44c57a3f5ca4b8fffc4db
Source dataset
uspto-grants-2003_04
Patent number
US06545000B1

Reaction notes

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