Sodium Carbonate → HCID 58456380, 화합물

HRID 1039930노트

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HRID 1039930 반응식
[Cl:1][C:2]1[N:7]=[C:6](Cl)[CH:5]=[CH:4][N:3]=1.C(=O)([O-])[O-].[Na+].[Na+].CC(O)(/C=C/B1O[C:23](C)([CH3:25])[C:22]([CH3:28])([CH3:27])[O:21]1)C>O1CCOCC1>[Cl:1][C:2]1[N:7]=[C:6](/[CH:25]=[CH:23]/[C:22]([CH3:28])([OH:21])[CH3:27])[CH:5]=[CH:4][N:3]=1

참가 물질

5

반응물 3

HCID 10340Sodium CarbonateHCID 775312,4-DichloropyrimidineHCID 11117347(E)-2-Methyl-4-(4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)but-3-en-2-ol

생성물 1

HCID 58456380HCID 58456380, 화합물

시약·촉매·용매 1

HCID 312751,4-Dioxane용매

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온도
90 °C

실험 절차

To a solution of 2,4-dichloropyrimidine (71 mg, 0.476 mmol) in dioxane (4 mL) and sodium carbonate (2M in water, 0.25 mL, 0.5 mmol) were added (3E)-2-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)but-3-en-2-ol (100 mg, 0.476 mmol) and tetrakis triphenylphosphine palladium(0) (55 mg, 0.048 mmol). The solution was degassed by bubbling nitrogen gas and heated to 90° C. for 2 hr. The solution was diluted with EtOAc, washed with brine, dried with MgSO4, filtered, and concentrated to dryness. The residue was purified by flash chromatography on silica gel (0-100% EtOAc/hexanes) to afford (3E)-4-(2-chloropyrimidin-4-yl)-2-methylbut-3-en-2-ol as a colorless oil. MS ESI: [M+H]+ m/z 199.1. 1H NMR (500 MHz, CDCl3) δ 8.52 (d, J=5.1, 1H) 7.24 (d, J=15.6, 1H) 7.12 (d, J=5.1, 1H) 6.60 (d, J=15.6, 1H); 1.22 (s, 6H).

후처리

  1. customThe solution was degassed
  2. customby bubbling nitrogen gas
  3. additionThe solution was diluted with EtOAc
  4. washwashed with brine
  5. dry with materialdried with MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated to dryness
  8. customThe residue was purified by flash chromatography on silica gel (0-100% EtOAc/hexanes)

출처 및 근거

ORD 기록
ord-669eab852f654a8e8c550f1fbfac0b7b
출처 데이터셋
uspto-grants-2013_10
특허 번호
US08551984B2

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