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

HRID 595840
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인쇄 미리보기

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HRID 595840 반응식
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
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참가 물질

6

반응물 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

생성물 1

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

시약·촉매·용매 2

HCID 178418807
HCID 178418807, 화합물
촉매
HCID 80711,2-Dimethoxyethane용매

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온도
120 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-e82ed1e6ea9e4fdd8a2f4778c27de53b
출처 데이터셋
uspto-grants-2016_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09242996B2

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