Sodium Carbonate → HCID 67053566, compound

HRID 885745Notes

Reaction equation

HRID 885745 reaction equation
[Br:1]Br.[CH:3]1([C:6]2[N:7]([CH2:17][O:18][CH2:19][CH2:20][Si:21]([CH3:24])([CH3:23])[CH3:22])[CH:8]=[C:9]([C:11]3[CH:16]=[CH:15][N:14]=[CH:13][N:12]=3)[N:10]=2)[CH2:5][CH2:4]1.C([O-])([O-])=O.[Na+].[Na+]>C(Cl)Cl>[Br:1][C:8]1[N:7]([CH2:17][O:18][CH2:19][CH2:20][Si:21]([CH3:24])([CH3:23])[CH3:22])[C:6]([CH:3]2[CH2:4][CH2:5]2)=[N:10][C:9]=1[C:11]1[CH:16]=[CH:15][N:14]=[CH:13][N:12]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 24408BromineHCID 67053526HCID 67053526, compound

Product 1

HCID 67053566HCID 67053566, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Bromine was added to a cooled solution of 4-(2-cyclopropyl-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazol-4-yl)pyrimidine (1.36 g, 4.30 mmol) in DCM at 0° C. followed by saturated aqueous Na2CO3 solution (16 mL, 4.30 mmol). The reaction mixture was stirred for 3 hours at room temperature. After the reaction was judged complete by LCMS analysis, the reaction mixture was allowed to stand and partition. The resulting layers were separated and the aqueous layer was extracted with EtOAc (2×). The combine organic layers were washed with brine, dried (Na2SO4), and concentrated. The resulting residue was by flash chromatography using an EtOAc-hexanes gradient (20-80%) to give 4-(5-bromo-2-cyclopropyl-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazol-4-yl)pyrimidine (1.07 g, 2.71 mmol, 63%) as a yellow oil: LCMS(m/z): 395.0 (MH+), tR=1.09 minutes; 1H NMR (400 MHz, CDCl3) δ 0.00 (s, 9H) 0.80-1.50 (m, 4H) 2.06-2.25 (m, 1H) 3.49-3.65 (m, 2H) 6.05 (s, 2H) 7.95-8.07 (m, 1H) 8.82-8.94 (m, 1H) 9.27-9.34 (m, 1H).

Workup

  1. custompartition
  2. customThe resulting layers were separated
  3. extractionthe aqueous layer was extracted with EtOAc (2×)
  4. washThe combine organic layers were washed with brine
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-26fc0a6c83d84074b3cef8cc4f65d4a1
Source dataset
uspto-grants-2012_08
Patent number
US08242260B2

Reaction notes

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