Methylamine → 5-Bromo-3-(5-(4-((methylamino)methyl)phenyl)-1,3,4-oxadiazol-2-yl)pyrazin-2-amine

HRID 1959453Notes

Reaction equation

HRID 1959453 reaction equation
[Br:1][C:2]1[N:3]=[C:4]([C:9]2[O:10][C:11]([C:14]3[CH:19]=[CH:18][C:17]([CH2:20]Br)=[CH:16][CH:15]=3)=[N:12][N:13]=2)[C:5]([NH2:8])=[N:6][CH:7]=1.C([O-])([O-])=O.[Na+].[Na+].[CH3:28][NH2:29]>O1CCCC1.O>[Br:1][C:2]1[N:3]=[C:4]([C:9]2[O:10][C:11]([C:14]3[CH:19]=[CH:18][C:17]([CH2:20][NH:29][CH3:28])=[CH:16][CH:15]=3)=[N:12][N:13]=2)[C:5]([NH2:8])=[N:6][CH:7]=1

Participants

6

Reactant 3

HCID 6329MethylamineHCID 10340Sodium CarbonateHCID 580704675-Bromo-3-(5-(4-(bromomethyl)phenyl)-1,3,4-oxadiazol-2-yl)pyrazin-2-amine

Product 1

HCID 594716885-Bromo-3-(5-(4-((methylamino)methyl)phenyl)-1,3,4-oxadiazol-2-yl)pyrazin-2-amineYield 97%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
60 °C

Procedure

A suspension of 5-bromo-3-[5-[4-(bromomethyl)phenyl]-1,3,4-oxadiazol-2-yl]pyrazin-2-amine (2 g, 4.9 mmol) and Na2CO3 (1.55 g, 14.60 mmol) in tetrahydrofuran (30 mL) was treated with methanamine (3.6 mL of 2 M, 7.3 mmol) in THF. The reaction mixture was heated at 60° C. for 1 h. The reaction was cooled, diluted with water and the organic layer was extracted with dichloromethane. The organic layer was dried over Na2SO4, filtered and concentrated in vacuo to yield 5-bromo-3-(5-(4-((methylamino)methyl)phenyl)-1,3,4-oxadiazol-2-yl)pyrazin-2-amine (1.7 g, 97%) as a yellow solid, which was used without purification in the next step. LC/MS m/z 363.5 [M+H]+.

Workup

  1. temperatureThe reaction was cooled
  2. extractionthe organic layer was extracted with dichloromethane
  3. dry with materialThe organic layer was dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-466d8a6958a74ecf91a18a25395c72e8
Source dataset
uspto-grants-2013_04
Patent number
US08410112B2

Reaction notes

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