Potassium Carbonate → 2-(Methylthio)-4-((4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)methyl)pyrimidine

HRID 2175244Notes

Reaction equation

HRID 2175244 reaction equation
[CH3:1][C:2]1([CH3:14])[C:6]([CH3:8])([CH3:7])[O:5][B:4]([C:9]2[CH:10]=[N:11][NH:12][CH:13]=2)[O:3]1.[C:15](=O)([O-])[O-].[K+].[K+].BrC[C:23]1[CH:24]=[N:25][C:26]([S:29][CH3:30])=[N:27][CH:28]=1>CN(C=O)C.CCOC(C)=O>[CH3:30][S:29][C:26]1[N:25]=[C:24]([CH2:15][N:12]2[CH:13]=[C:9]([B:4]3[O:5][C:6]([CH3:7])([CH3:8])[C:2]([CH3:14])([CH3:1])[O:3]3)[CH:10]=[N:11]2)[CH:23]=[CH:28][N:27]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 27740104-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazoleHCID 60209911HCID 60209911, compound

Product 1

HCID 709823642-(Methylthio)-4-((4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)methyl)pyrimidineYield 70%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (0.5 g, 2.58 mmol), potassium carbonate (0.356 g, 2.58 mmol) and 5-(bromomethyl)-2-(methylthio)pyrimidine (30% in THF, 2.070 g, 2.83 mmol) in DMF (5 mL) was stirred at room temperature for 14 h. After this time, the reaction mixture was diluted with EtOAc, washed with saturated sodium bicarbonate, dried over anhydrous MgSO4, filtered, and concentrated. The resulting residue was purified by flash chromatography (0-100% ethyl acetate:hexanes) to afford the title compound (0.6 g, 70% yield) as a light yellow solid. LCMS, [M+H]+=333.2. 1H NMR (400 MHz, CDCl3) δ 8.43 (d, J=5.1 Hz, 1H), 7.87 (s, 1H), 7.81 (s, 1H), 6.49 (d, J=5.1 Hz, 1H), 5.36 (s, 2H), 2.56 (s, 3H), 1.33 (s, 12H).

Workup

  1. washwashed with saturated sodium bicarbonate
  2. dry with materialdried over anhydrous MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe resulting residue was purified by flash chromatography (0-100% ethyl acetate:hexanes)

Sources & evidence

ORD record
ord-b1135a91db0e49a8857af47de88e6a68
Source dataset
uspto-grants-2015_06
Patent number
US09062028B2

Reaction notes

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