Water → 5-[4-(Methylsulfonyl)phenyl]-2-pyrazinamine

HRID 2174653노트

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HRID 2174653 반응식
Br[C:2]1[C:3]([NH2:8])=[N:4][CH:5]=[CH:6][N:7]=1.[CH3:9][S:10]([C:13]1[CH:18]=[CH:17][C:16](B(O)O)=[CH:15][CH:14]=1)(=[O:12])=[O:11].[O-]P([O-])([O-])=O.[K+].[K+].[K+].O>CC#N.CC(C)([P](C(C)(C)C)([Pd][P](C(C)(C)C)(C(C)(C)C)C(C)(C)C)C(C)(C)C)C>[CH3:9][S:10]([C:13]1[CH:18]=[CH:17][C:16]([C:6]2[N:7]=[CH:2][C:3]([NH2:8])=[N:4][CH:5]=2)=[CH:15][CH:14]=1)(=[O:12])=[O:11]

참가 물질

7

반응물 4

HCID 962WaterHCID 62657Potassium Phosphate, TribasicHCID 27343644-(Methanesulfonyl)phenylboronic acidHCID 147359423-Bromopyrazin-2-amine

생성물 1

HCID 580843845-[4-(Methylsulfonyl)phenyl]-2-pyrazinamine수율 88%

시약·촉매·용매 2

HCID 178418851HCID 178418851, 화합물촉매HCID 6342Acetonitrile용매

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온도
60 °C

실험 절차

Bromopyrazin-2-amine (2.0 g, 11.49 mmol), (4-methylsulfonylphenyl)boronic acid (2.758 g, 13.79 mmol) and K3PO4 (4.878 g, 22.98 mmol) were combined in MeCN (40 mL)/Water (10 mL) and Pd[P(tBu)3]2 (216 mg, 0.4227 mmol) was added. The reaction was heated at 60° C. for 1 hour. The reaction mixture was cooled to ambient temperature and concentrated in vacuo. The residue was triturated with water, then Et2O then dried in vacuo to give the sub-title compound as a beige solid which was used without further purification (2.53 g, 88% Yield). 1H NMR (400.0 MHz, DMSO) δ 3.20 (s, 3H), 6.80 (br s, 2H), 7.94 (d, 2H), 8.00 (d, 1H), 8.17 (d, 2H) and 8.64 (d, 1H) ppm.

후처리

  1. additionwas added
  2. temperatureThe reaction mixture was cooled to ambient temperature
  3. concentrationconcentrated in vacuo
  4. customThe residue was triturated with water
  5. dry with materialEt2O then dried in vacuo

출처 및 근거

ORD 기록
ord-0a54bdf31d354acba02ca2bfe5ef6e3a
출처 데이터셋
uspto-grants-2015_06
특허 번호
US09062008B2

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