Sodium Carbonate → 2-Chloro-4-(thiophen-2-yl)pyrimidine

HRID 2267350Notes

Reaction equation

HRID 2267350 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1B(O)O.C([O-])([O-])=O.[Na+].[Na+].[Cl:15][C:16]1[N:21]=[C:20](Cl)[CH:19]=[CH:18][N:17]=1>CC#N.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:15][C:16]1[N:21]=[C:20]([C:2]2[S:1][CH:5]=[CH:4][CH:3]=2)[CH:19]=[CH:18][N:17]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 775312,4-DichloropyrimidineHCID 27339602-Thiopheneboronic acid

Product 1

HCID 141179412-Chloro-4-(thiophen-2-yl)pyrimidine

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 6342AcetonitrileSolvent

Procedure

A solution of 2.0 g (15.6 mmol) of 2-thiopheneboronic acid in 80 mL of a 5% (w/v) Na2CO3 aqueous solution was added drop wise to a refluxing solution of 4.7 g (31 mmol) of 2,4-dichloropyrimidine and 0.55 g (0.78 mmol) of bis(triphenylphosphine)palladium(II) chloride in 80 mL of MeCN. The reaction solution was heated at reflux for 6 h, then cooled to rt, the organic solvent removed in vacuo, and the resulting purple solid filtered and washed with water. The crude product was purified by flash chromatography eluting with a linear gradient of neat hexane to neat EtOAc to deliver the title compound. MS (M+H)+ 197.

Workup

  1. temperatureThe reaction solution was heated
  2. temperatureat reflux for 6 h
  3. customthe organic solvent removed in vacuo
  4. filtrationthe resulting purple solid filtered
  5. washwashed with water
  6. customThe crude product was purified by flash chromatography
  7. washeluting with a linear gradient of neat hexane to neat EtOAc

Sources & evidence

ORD record
ord-2d254bcd851847f8b6d48af0b4e59a22
Source dataset
uspto-grants-2010_12
Patent number
US07858785B2

Reaction notes

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