Sodium Carbonate → HCID 58456380, compound

HRID 410439Notes

Reaction equation

HRID 410439 reaction equation
[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

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 775312,4-DichloropyrimidineHCID 11117347581802-26-8

Product 1

HCID 58456380HCID 58456380, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
90 °C

Procedure

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).

Workup

  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)

Sources & evidence

ORD record
ord-b8245dda30574070a2d40f02df856aac
Source dataset
uspto-grants-2014_06
Patent number
US08759366B2

Reaction notes

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