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Sodium Carbonate → 5-(2-methyl-3,6-dihydro-2H-pyran-4-yl)pyrazin-2-amine

HRID 595840
ノート
印刷プレビュー

反応式

HRID 595840 の反応式
FC(F)(F)S(O[C:7]1[CH2:8][CH:9]([CH3:13])[O:10][CH2:11][CH:12]=1)(=O)=O.CC1(C)C(C)(C)OB([C:24]2[N:25]=[CH:26][C:27]([NH2:30])=[N:28][CH:29]=2)O1.C([O-])([O-])=O.[Na+].[Na+]>COCCOC.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].C(Cl)Cl>[CH3:13][CH:9]1[CH2:8][C:7]([C:24]2[N:25]=[CH:26][C:27]([NH2:30])=[N:28][CH:29]=2)=[CH:12][CH2:11][O:10]1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

HCID 10340Sodium CarbonateHCID 179989875-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyrazin-2-amineHCID 1180454962-methyl-3,6-dihydro-2H-pyran-4-yl trifluoromethanesulfonate

生成物 1

HCID 1180453955-(2-methyl-3,6-dihydro-2H-pyran-4-yl)pyrazin-2-amine収率 45.4%

試薬・触媒・溶媒 2

HCID 178418807HCID 178418807、化合物
触媒
HCID 80711,2-Dimethoxyethane溶媒

反応条件

温度
120 °C

実験手順

To a solution of 2-methyl-3,6-dihydro-2H-pyran-4-yl trifluoromethanesulfonate (0.637 g, 2.88 mmol), 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrazin-2-amine (0.914 g, 3.74 mmol), and PdCl2(dppf)-CH2Cl2 adduct (0.235 g, 0.288 mmol) in DME (9.82 mL) was added 2M Na2CO3 (3.27 mL). The reaction mixture was heated at microwave synthesizer (120° C., 10 min). Ethyl acetated was added, and washed with sat NaHCO3, and water. Then the desired compound was extracted to 1N HCl aqueous layer, and washed with EtOAc. Basified with 2N NaOH, and the product was extracted to EtOAc layer. EtOAc organic layer was washed with water and dried over Na2SO4. Filtered and concentrated to provide 250 mg of desired compound. LCMS (m/z): 192.2 (MH+), 0.40 min.

後処理

  1. additionEthyl acetated was added
  2. washwashed
  3. extractionThen the desired compound was extracted to 1N HCl aqueous layer
  4. washwashed with EtOAc
  5. extractionBasified with 2N NaOH, and the product was extracted to EtOAc layer
  6. washEtOAc organic layer was washed with water
  7. dry with materialdried over Na2SO4
  8. filtrationFiltered
  9. concentrationconcentrated

出典と根拠

ORDレコード
ord-e82ed1e6ea9e4fdd8a2f4778c27de53b
出典データセット
uspto-grants-2016_01
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09242996B2

反応ノート

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