Water → HCID 66520377, compound

HRID 472641Notes

Reaction equation

HRID 472641 reaction equation
Cl[C:2]1[N:7]=[C:6]([NH2:8])[CH:5]=[N:4][CH:3]=1.[CH3:9][N:10]1[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]1.O>CN(C)C=O>[CH3:9][N:10]1[CH2:15][CH2:14][N:13]([C:2]2[CH:3]=[N:4][CH:5]=[C:6]([NH2:8])[N:7]=2)[CH2:12][CH2:11]1

Participants

5

Reactant 3

HCID 962WaterHCID 531671-MethylpiperazineHCID 1184582-Amino-6-Chloropyrazine

Product 1

HCID 66520377HCID 66520377, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

4-Methyl-3,4,5,6-tetrahydro-2H-[1,2′]bipyrazinyl-6′-ylamine was prepared from 6-chloro-pyrazin-2-ylamine (1.00 g, 7.72 mmol) and 1-methylpiperazine (942 L, 8.49 mmol) combined in N,N-dimethylformamide (35 mL) and heated at 100° C. overnight. The reaction was poured into water and extracted with 3 portions of dichloromethane. The combined organic was dried over magnesium sulfate, filtered and evaporated to yield an off-white solid. This solid was purified via chromatography (silica gel 40 g methanol in dichloromethane). Product isolated as a tan oil that solidified upon standing. 1H NMR (400 MHz, (D3C)2SO, δ, ppm):7.33 (s, 1H), 7.16 (s, 1H), 5.93 (s, 2H), 3.40 (s, 4H), 2.36 (s, 4H), 2.20 (s, 3H).

Workup

  1. extractionextracted with 3 portions of dichloromethane
  2. dry with materialThe combined organic was dried over magnesium sulfate
  3. filtrationfiltered
  4. customevaporated
  5. customto yield an off-white solid
  6. customThis solid was purified via chromatography (silica gel 40 g methanol in dichloromethane)
  7. customProduct isolated as a tan oil that

Sources & evidence

ORD record
ord-eed5016526a44de5ab1f2db97b49b9b2
Source dataset
uspto-grants-2014_01
Patent number
US08633173B2

Reaction notes

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