Acetic Acid → (5-bromo-pyrazin-2-yl)-(1,3-dimethyl-1H-pyrazol-4-ylmethyl)amine

HRID 1958591Notes

Reaction equation

HRID 1958591 reaction equation
[CH3:1][N:2]1[CH:6]=[C:5]([CH:7]=O)[C:4]([CH3:9])=[N:3]1.[NH2:10][C:11]1[CH:16]=[N:15][C:14]([Br:17])=[CH:13][N:12]=1.[B-][N+](C)(C)C.C(O)(=O)C>C(OCC)(=O)C>[Br:17][C:14]1[N:15]=[CH:16][C:11]([NH:10][CH2:7][C:5]2[C:4]([CH3:9])=[N:3][N:2]([CH3:1])[CH:6]=2)=[N:12][CH:13]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 5995392-Amino-5-bromopyrazineHCID 8472851,3-dimethyl-1H-pyrazole-4-carbaldehydeHCID 6327651Borane,N-dimethylmethanamine (1:1)

Product 1

HCID 86614303(5-bromo-pyrazin-2-yl)-(1,3-dimethyl-1H-pyrazol-4-ylmethyl)amineYield 92.9%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 1,3-dimethyl-1H-pyrazole-4-carbaldehyde (142 mg, 1.145 mmol), 2-amino-5-bromopyrazine (200 mg, 1.149 mmol), borane trimethylamine complex (126 mg, 1.73 mmol) and glacial acetic acid (137 mg, 2.29 mmol) in anhydrous methonol (3 ml) was stirred at room temperature overnight. The reaction mixture was then diluted with ethyl acetate, washed with water, dried over MgSO4 and filtered. The filtrate was concentrated to give 300 mg of (5-bromo-pyrazin-2-yl)-(1,3-dimethyl-1H-pyrazol-4-ylmethyl)amine as crude product, which was used for next step reaction without further purification. Crude yield: 93%.

Workup

  1. washwashed with water
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-d31f5667466b43db91b5932cf3a42704
Source dataset
uspto-grants-2013_04
Patent number
US08410121B2

Reaction notes

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