Phosphorus oxychloride → HCID 86707955, compound

HRID 1526502Notes

Reaction equation

HRID 1526502 reaction equation
O[C:2]1[C:3]2[C:10]3[CH:11]=[C:12]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH:13]=[CH:14][C:9]=3[S:8][C:4]=2[N:5]=[CH:6][N:7]=1.O=P(Cl)(Cl)[Cl:22]>O1CCOCC1>[Cl:22][C:2]1[C:3]2[C:10]3[CH:11]=[C:12]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH:13]=[CH:14][C:9]=3[S:8][C:4]=2[N:5]=[CH:6][N:7]=1

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178468702HCID 178468702, compound

Product 1

HCID 86707955HCID 86707955, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
90 °C

Procedure

Into a 100-mL round-bottom flask containing a solution of ethyl 4-hydroxybenzo[4,5]thieno[2,3-d]pyrimidine-6-carboxylate (2.2 g, 4.01 mmol, 1.00 equiv) in 1,4-dioxane (60 mL) was added POCl3 (30 mL) at room temperature under nitrogen. The resulting solution was stirred for 2 h at 90° C. and concentrated under vacuum. The residue dissolved in DCM and poured into a cooled saturated aqueous Na2CO3, extracted with 3×100 mL of dichloromethane. The combined organic layers were washed with brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was applied onto a silica gel column with ethyl acetate/petroleum ether (1:9) to give 1.8 g (77%) of the corresponding ethyl 4-chlorobenzo[4,5]thieno[2,3-d]pyrimidine-6-carboxylate as a yellow solid.

Workup

  1. concentrationconcentrated under vacuum
  2. dissolutionThe residue dissolved in DCM
  3. additionpoured into a cooled saturated aqueous Na2CO3
  4. extractionextracted with 3×100 mL of dichloromethane
  5. washThe combined organic layers were washed with brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-2eb7063019c7432aadd5f6e8d3802844
Source dataset
uspto-grants-2015_07
Patent number
US09085586B2

Reaction notes

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