Sodium Carbonate → 4-Chloro-6-(2-fluorophenyl)pyrimidine

HRID 1751982Notes

Reaction equation

HRID 1751982 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6](Cl)[N:5]=[CH:4][N:3]=1.[F:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1B(O)O.C([O-])([O-])=O.[Na+].[Na+].C(OCC)(=O)C.CCCCCC>C(COC)OC.O.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[Cl:1][C:2]1[CH:7]=[C:6]([C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[F:9])[N:5]=[CH:4][N:3]=1

Participants

7

Reactant 4

HCID 10340Sodium CarbonateHCID 709434,6-DichloropyrimidineHCID 27343542-Fluorophenylboronic acidHCID 21226206Ethyl acetate hexane

Product 1

HCID 225998154-Chloro-6-(2-fluorophenyl)pyrimidine

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 18180031Water 1,2-dimethoxyethaneSolvent

Procedure

4,6-dichloropyrimidine (5.1 g, 34.1 mmol), 2-fluorophenyl boronic acid (5.0 g, 35.7 mmol, 1.05 equiv), Na2CO3 (6.9 g, 65.0 mmol, 1.8 equiv) and Pd(PPh3)2Cl2 (0.3 g, 0.4 mmol, 0.01 equiv) were refluxed in dimethoxyethane-water (204:69 mL) mixed solvent system for 4 h. Reaction was monitored by tlc (using ethyl acetate-hexane, 1:9). Reaction mixture was cooled and the subject compound was extracted using dichloromethane. Subject compound was purified by flash chromatography (2.5% ethyl acetate in n-hexane) to yield 3.7 g (Yield=52.0%).

Workup

  1. additionmixed solvent system for 4 h
  2. customReaction
  3. customReaction mixture
  4. temperaturewas cooled
  5. extractionthe subject compound was extracted
  6. customSubject compound was purified by flash chromatography (2.5% ethyl acetate in n-hexane)
  7. customto yield 3.7 g (Yield=52.0%)

Sources & evidence

ORD record
ord-c6b714b628f4465ebb03710385d0b79d
Source dataset
uspto-grants-2015_10
Patent number
US09162987B2

Reaction notes

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