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Sodium Carbonate → 3-Amino-6-(pyridin-3-yl)pyrazine-2-carboxylic acid

HRID 78564
ノート
印刷プレビュー

反応式

HRID 78564 の反応式
[NH2:1][C:2]1[C:3]([C:9]([O:11]C)=[O:10])=[N:4][C:5](Br)=[CH:6][N:7]=1.C(B(CC)[C:16]1[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=1)C.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(=O)([O-])[O-].[Na+].[Na+]>COCCOC.Cl[Pd]Cl.CCOC(C)=O>[NH2:1][C:2]1[C:3]([C:9]([OH:11])=[O:10])=[N:4][C:5]([C:16]2[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=2)=[CH:6][N:7]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

8

反応物 4

HCID 10340Sodium CarbonateHCID 11776TriphenylphosphineHCID 227251Methyl 3-Amino-6-bromopyrazine-2-carboxylateHCID 6428513-(Diethylboryl)pyridine

生成物 1

HCID 594721543-Amino-6-(pyridin-3-yl)pyrazine-2-carboxylic acid収率 83.4%

試薬・触媒・溶媒 3

HCID 24290
Palladium Chloride
触媒
HCID 80711,2-Dimethoxyethane溶媒
HCID 8857Ethyl Acetate溶媒

実験手順

A mixture of methyl 3-amino-6-bromo-pyrazine-2-carboxylate (8 g, 34.48 mmol), diethyl-(3-pyridyl)borane (6.084 g, 41.38 mmol), dichloropalladium; triphenylphosphane (1.210 g, 1.724 mmol) and disodium carbonate (51.70 mL of 2 M, 103.4 mmol) in DME (100 mL) were heated overnight at 80° C. The reaction mixture was cooled and EtOAc was added. The resultant precipitate was collected, treated with water and the resultant suspension heated and filtered hot. The solution was then allowed to cool and acidified with AcOH to approx pH 5. The precipitate was collected, washed with MeOH and dried to yield the product as a yellow powder (6.22 g, 83% Yield). 1H NMR (400.0 MHz, DMSO) d 7.49 (dd, J=4.8, 7.4 Hz, 1H), 7.60 (s, 2H), 8.44 (d, J=7.6 Hz, 1H), 8.57 (d, J=3.7 Hz, 1H), 8.97 (s, 1H) and 9.27 (s, 1H) ppm; MS (ES+) 217

後処理

  1. temperatureThe reaction mixture was cooled
  2. customThe resultant precipitate was collected
  3. additiontreated with water
  4. temperaturethe resultant suspension heated
  5. filtrationfiltered hot
  6. temperatureto cool
  7. customThe precipitate was collected
  8. washwashed with MeOH
  9. customdried

出典と根拠

ORDレコード
ord-90c9a609f1164fa2800eafbbc9caf6e9
出典データセット
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08841308B2

反応ノート

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