Ammonium Chloride → HCID 90408787, compound

HRID 2177631Notes

Reaction equation

HRID 2177631 reaction equation
[NH2:1][C:2]1[CH:7]=[N:6][CH:5]=[CH:4][N:3]=1.CC(C)([O-])C.[K+].[Cl:14][C:15]1[C:20]([N+:21]([O-:23])=[O:22])=[C:19](Cl)[CH:18]=[C:17]([CH3:25])[N:16]=1.[NH4+].[Cl-]>CS(C)=O>[Cl:14][C:15]1[C:20]([N+:21]([O-:23])=[O:22])=[C:19]([NH:1][C:2]2[CH:7]=[N:6][CH:5]=[CH:4][N:3]=2)[CH:18]=[C:17]([CH3:25])[N:16]=1

Participants

6

Reactant 4

HCID 25517Ammonium ChlorideHCID 78747AminopyrazineHCID 27848192,4-Dichloro-6-methyl-3-nitropyridineHCID 23665647Potassium tert-butoxide

Product 1

HCID 90408787HCID 90408787, compoundYield 23%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of 2-aminopyrazine (0.900 g, 9.47 mmol) in DMSO (40 mL) was added potassium tert-butoxide (2.13 g, 18.9 mmol) followed by 2,4-dichloro-6-methyl-3-nitropyridine (2.00 g, 9.47 mmol). After stirring for 30 min at rt, sat. NH4Cl solution was added. The organic layer was separated and the water layer was extracted with CH2Cl2 three times. The combined organic layers were dried over anhydrous Na2SO4, filtered and concentrated. Chromatography on silica gel (0-70% ethyl acetatehexanes) provided the desired product (567 mg, 23%). MS (ESI) mass calcd. C10H8ClN5O2, 265.04. m/z found, 266.0 [M+H]+. 1H NMR (500 MHz, CDCl3) δ 8.69-8.62 (br s, 1H), 8.38-8.34 (m, 2H), 8.34-8.29 (m, 2H), 2.59-2.56 (m, 3H).

Workup

  1. customThe organic layer was separated
  2. extractionthe water layer was extracted with CH2Cl2 three times
  3. dry with materialThe combined organic layers were dried over anhydrous Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-cd8bec73f5804955b0443f7eadde8358
Source dataset
uspto-grants-2015_06
Patent number
US09066946B2

Reaction notes

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