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

HRID 469864ノート

反応式

HRID 469864 の反応式
[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

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

実験手順

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%.

後処理

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

出典と根拠

ORDレコード
ord-a69eecf819694654a0b6d7451991e35e
出典データセット
uspto-grants-2014_01
特許番号
US08629156B2

反応ノート

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