Sodium Carbonate → HCID 90110263, compound

HRID 1508897Notes

Reaction equation

HRID 1508897 reaction equation
Cl[C:2]1[CH:7]=[C:6]([CH2:8][CH3:9])[N:5]=[C:4]([C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([Cl:16])[CH:11]=2)[N:3]=1.[CH3:17][C:18]([C:24]1[CH:29]=[CH:28][C:27]([CH2:30]B2OC(C)(C)C(C)(C)O2)=[CH:26][CH:25]=1)([CH3:23])[C:19]([O:21][CH3:22])=[O:20].C([O-])([O-])=O.[Na+].[Na+].O1CCOCC1>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].O>[Cl:16][C:12]1[CH:11]=[C:10]([C:4]2[N:3]=[C:2]([CH2:30][C:27]3[CH:26]=[CH:25][C:24]([C:18]([CH3:17])([CH3:23])[C:19]([O:21][CH3:22])=[O:20])=[CH:29][CH:28]=3)[CH:7]=[C:6]([CH2:8][CH3:9])[N:5]=2)[CH:15]=[CH:14][CH:13]=1

Participants

7

Reactant 4

HCID 10340Sodium CarbonateHCID 312751,4-DioxaneHCID 435575804-Chloro-2-(3-chlorophenyl)-6-ethylpyrimidineHCID 90338678HCID 90338678, compound

Product 1

HCID 90110263HCID 90110263, compoundYield 96%

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

A 20-mL sealed tube, with stirrer bar, was charged with 4-chloro-2-(3-chlorophenyl)-6-ethylpyrimidine (0.303 g, 1.20 mol), methyl 2-methyl-2-(4-((4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)methyl)phenyl)propanoate (0.420 g, 1.32 mmol), Pd(dppf)Cl2 (0.098 g, 0.12 mmol), and powdered Na2CO3 (0.380 g, 3.60 mmol). Dioxane (6 mL) and water (3 mL) were added. The resulting mixture was stirred under Ar at 90° C. for 2 h. After this time, the mixture was cooled to room temperature and filtered through celite washing with ethyl acetate until the filtrate was colorless. The filtrate was washed with saturated sodium chloride (3×25 mL) then dried over sodium sulfate, filtered, and concentrated under reduced pressure. The residue (0.87 g) was purified by chromatography on silica using hexane/dichloromethane (10:0 to 8:2) as eluent to afford the title compound (0.47 g, 96%) as a colorless oil. MW=408.92. 1H NMR (CDCl3, 300 MHz) δ 8.50-8.47 (m, 1H), 8.40-8.35 (m, 1H), 7.46-7.37 (m, 2H), 7.31-7.24 (m, 4H), 6.87 (s, 1H), 4.10 (s, 2H), 3.65 (s, 3H), 2.77 (q, J=7.8 Hz, 2H), 1.57 (s, 6H), 1.32 (t, J=7.5 Hz, 3H); ESI MS m/z 409 [M+H]+.

Workup

  1. customA 20-mL sealed tube
  2. temperatureAfter this time, the mixture was cooled to room temperature
  3. filtrationfiltered
  4. washthrough celite washing with ethyl acetate until the filtrate
  5. washThe filtrate was washed with saturated sodium chloride (3×25 mL)
  6. dry with materialthen dried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customThe residue (0.87 g) was purified by chromatography on silica

Sources & evidence

ORD record
ord-bd2c6a1d7ed04473a8bd69c9eb086454
Source dataset
uspto-grants-2015_12
Patent number
US09221843B2

Reaction notes

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