N,N-Dimethylaniline → HCID 58169158, compound

HRID 1484890Notes

Reaction equation

HRID 1484890 reaction equation
[Cl:1][C:2]1[C:3](O)=[N:4][C:5]([C:8]2[S:9][CH:10]=[CH:11][CH:12]=2)=[N:6][CH:7]=1.P(Br)(Br)([Br:16])=O.CN(C)C1C=CC=CC=1>C1(C)C=CC=CC=1>[Br:16][C:3]1[C:2]([Cl:1])=[CH:7][N:6]=[C:5]([C:8]2[S:9][CH:10]=[CH:11][CH:12]=2)[N:4]=1

Participants

5

Reactant 3

HCID 949N,N-DimethylanilineHCID 24613Phosphorus oxybromideHCID 178517530HCID 178517530, compound

Product 1

HCID 58169158HCID 58169158, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 5-chloro-2-(thiophen-2-yl)pyrimidin-4-ol (90 mg, 0.42 mmol, 1.0 equiv.), POBr3 (364 mg, 1.27 mmol, 3.0 equiv.) and N,N-dimethylbenzenamine (103 mg, 0.85 mmol, 2.0 equiv.) in toluene (5 mL) was stirred at 100° C. for 1 h, then poured into crashed ice. The mixture was extracted with ethyl acetate. The combined organic layers were washed over saturated NaHCO3, brine, dried over Na2SO4, filtered and concentrated. The residue was purified by column chromatography to afford 4-bromo-5-chloro-2-(thiophen-2-yl)pyrimidine, which was directly used for the next step. LC-MS (m/z)=275.0 [M+H]+.

Workup

  1. additionpoured
  2. extractionThe mixture was extracted with ethyl acetate
  3. washThe combined organic layers were washed over saturated NaHCO3, brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-530701316d504535aeff780f36d765e0
Source dataset
uspto-grants-2016_08
Patent number
US09422271B2

Reaction notes

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