Water → HCID 66927641, compound

HRID 1039072Notes

Reaction equation

HRID 1039072 reaction equation
Cl[C:2]1[N:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][N:3]=1.[NH:11]1[CH:15]=[N:14][N:13]=[N:12]1.C(N(CC)CC)C.O>CN(C=O)C>[N+:8]([C:5]1[CH:4]=[N:3][C:2]([N:11]2[CH:15]=[N:14][N:13]=[N:12]2)=[N:7][CH:6]=1)([O-:10])=[O:9]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 825442-Chloro-5-nitropyrimidineHCID 178418441HCID 178418441, compound

Product 1

HCID 66927641HCID 66927641, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

2-chloro-5-nitropyrimidine (1.6 g, 10 mmol), 1H-tetrazole (24.44 mL, 11 mmol, 0.45M in MeCN) were added in DMF (20 mL), cooled to 0° C., then triethylamine (1.67 mL, 12 mmol) was added drop-wise. After 15 minutes, water (100 mL) was added, extracted with ethyl acetate (100 mL×1, 50 mL×6). The organic phase were combined and dried by magnesium sulfate, filtered, concentrated and purified by column chromatography through a 100 gram Biotage SNAP KP-Sil™silica gel cartridge eluting with 30% ethyl acetate/hexanes to give the title compound as a pale yellow solid.

Workup

  1. extractionextracted with ethyl acetate (100 mL×1, 50 mL×6)
  2. dry with materialdried by magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. custompurified by column chromatography through a 100 gram Biotage SNAP KP-Sil™silica gel cartridge
  6. washeluting with 30% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-8f8d75c9b70e480494b77c9c5ddbb215
Source dataset
uspto-grants-2013_10
Patent number
US08552022B2

Reaction notes

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