Dimethylformamide → HCID 57907656, compound

HRID 1968456Notes

Reaction equation

HRID 1968456 reaction equation
[Br:1][C:2]1[CH:3]=[N:4][C:5]([C:8]2[CH:9]=[CH:10][C:11](=[O:14])[NH:12][N:13]=2)=[N:6][CH:7]=1.C(=O)([O-])[O-].[K+].[K+].CN(C=O)C.CS(O[CH2:31][C:32]#[C:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH3:40])(=O)=O>O>[Br:1][C:2]1[CH:7]=[N:6][C:5]([C:8]2[CH:9]=[CH:10][C:11](=[O:14])[N:12]([CH2:31][C:32]#[C:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH3:40])[N:13]=2)=[N:4][CH:3]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 57907660HCID 57907660, compoundHCID 57907672HCID 57907672, compound

Product 1

HCID 57907656HCID 57907656, compoundYield 12,843.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a 20 mL 1 neck flask equipped with magnetic stirrer, and nitrogen inlet was charged 30 milligrams (mg) of 6-(5-bromopyrimidin-2-yl)pyridazin-3(2H)-one (0.12 mmol), 33 mg of potassium carbonate (0.24 mmol), and 5 mL of dry DMF. The reaction mixture was stirred for about 30 minutes at ambient temperature followed by the addition of 100 mg of dec-2-ynyl methanesulfonate (0.43 mmol) in one portion. The reaction was stirred overnight at ambient temperature. The reaction was poured into about 10 mL of water, and extracted with 3×10 mL of ethyl acetate. The combined organic extract was washed with 10 mL of water, 10 mL of saturated aqueous sodium chloride solution, dried, and stripped to the crude product which was purified by silica gel column chromatography (20% ethyl acetate/80% hexanes). The pure fractions were combined and concentrated under vacuum on a rotary evaporator to afford 6 g of a white solid consistent with the title compound upon analysis by NMR. The NMR data is as follows: 300 MHz 1H NMR (CDCl3, TMS=0 ppm) 0.85 (m 3H); 1.25 (m, 6H); 1.60-1.65 (m, 4H); 2.15 (m, 2H); 5.05 (s, 2H); 7.05 (d, 1H); 8.35 (d, 1H); 9.00 (s, 2H).

Workup

  1. stirringThe reaction was stirred overnight at ambient temperature
  2. extractionextracted with 3×10 mL of ethyl acetate
  3. extractionThe combined organic extract
  4. washwas washed with 10 mL of water, 10 mL of saturated aqueous sodium chloride solution
  5. customdried
  6. customwas purified by silica gel column chromatography (20% ethyl acetate/80% hexanes)
  7. concentrationconcentrated under vacuum on a rotary evaporator

Sources & evidence

ORD record
ord-224fb2fa567f43eca2dffa7fbaedf4db
Source dataset
uspto-grants-2013_04
Patent number
US08426412B2

Reaction notes

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