N,N'-Dimethylethylenediamine → 3-(4-Azido-benzyl)-2-ethyl-5,7-dimethyl-pyrazolo[1,5-a]pyrimidine

HRID 403496Notes

Reaction equation

HRID 403496 reaction equation
Br[C:2]1[CH:21]=[CH:20][C:5]([CH2:6][C:7]2[C:8]([CH2:18][CH3:19])=[N:9][N:10]3[C:15]([CH3:16])=[CH:14][C:13]([CH3:17])=[N:12][C:11]=23)=[CH:4][CH:3]=1.[N-:22]=[N+:23]=[N-:24].[Na+].CNCCNC.O=C1O[C@H]([C@H](CO)O)C([O-])=C1O.[Na+]>C(O)C.CCOC(C)=O.[Cu]I.O>[N:22]([C:2]1[CH:21]=[CH:20][C:5]([CH2:6][C:7]2[C:8]([CH2:18][CH3:19])=[N:9][N:10]3[C:15]([CH3:16])=[CH:14][C:13]([CH3:17])=[N:12][C:11]=23)=[CH:4][CH:3]=1)=[N+:23]=[N-:24]

Participants

9

Reactant 4

HCID 8070N,N'-DimethylethylenediamineHCID 33557Sodium AzideHCID 23667548Sodium AscorbateHCID 683789033-(4-Bromobenzyl)-2-ethyl-5,7-dimethylpyrazolo[1,5-A]pyrimidine

Product 1

HCID 866717563-(4-Azido-benzyl)-2-ethyl-5,7-dimethyl-pyrazolo[1,5-a]pyrimidine

Reagents, catalysts & solvents 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 702EthanolSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

A vial containing 3-(4-bromo-benzyl)-2-ethyl-5,7-dimethyl-pyrazolo[1,5-a]pyrimidine (3) (10 g, 29.0 mmol), sodium azide (3.78 g, 58.1 mmol), copper(I) iodide (0.553 g, 2.90 mmol), N,N′-dimethylethylenediamine (0.469 ml, 4.36 mmol) and sodium ascorbate (0.288 g, 1.452 mmol) in ethanol (45 ml)/water (15.00 ml) was submitted to microwave irradiations for 1 h at 100° C. The reaction was diluted with EtOAc and washed with sat aqu Na2 CO3, water and brine. The organic layer was dried over anhydrous Na2 SO4, filtered and concentrated under HV. The crude product was purified by flash chromatography (silica gel, EtOAc/heptane 5% to 40%) to give a pale yellow solid.

Workup

  1. customfor 1 h
  2. customat 100° C
  3. washwashed
  4. customThe organic layer was dried over anhydrous Na2 SO4
  5. filtrationfiltered
  6. concentrationconcentrated under HV
  7. customThe crude product was purified by flash chromatography (silica gel, EtOAc/heptane 5% to 40%)
  8. customto give a pale yellow solid

Sources & evidence

ORD record
ord-480f73c0cac34404a448a6deca0b8c2c
Source dataset
uspto-grants-2014_06
Patent number
US08748435B2

Reaction notes

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