Phosphorus oxychloride → 4-chloro-6-ethylthieno[2,3-d]pyrimidine

HRID 2369407Notes

Reaction equation

HRID 2369407 reaction equation
[CH2:1]([C:3]1[S:12][C:6]2[N:7]=[CH:8][N:9]=[C:10](O)[C:5]=2[CH:4]=1)[CH3:2].O=P(Cl)(Cl)[Cl:15]>O1CCCCO1>[Cl:15][C:10]1[C:5]2[CH:4]=[C:3]([CH2:1][CH3:2])[S:12][C:6]=2[N:7]=[CH:8][N:9]=1

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178435421HCID 178435421, compound

Product 1

HCID 9161764-chloro-6-ethylthieno[2,3-d]pyrimidineYield 64%

Reagents, catalysts & solvents 1

HCID 1385701,2-DioxaneSolvent

Procedure

To a solution of 6-ethylthieno[2,3-d]pyrimidin-4-ol (10 g, 55.49 mmol, 1.00 equiv) in 1,2-dioxane (100 mL) was added POCl3 (30 mL) and heated to reflux for 4 hr. After completion of the reaction, the reaction mixture was concentrated under vacuum and then quenched with water/ice. The resulting solution was extracted with 3×200 mL of ethyl acetate: The combined organic layers were washed with brine, dried over anhydrous sodium sulfateand concentrated under vacuum. The residue was purified on a silica gel column with ethyl acetate/petroleum ether (1/10) to give 7 g (64%) of 4-chloro-6-ethylthieno[2,3-d]pyrimidine as a yellow solid. MS (ES, m/z): 382 (M+H+).

Workup

  1. temperatureheated
  2. temperatureto reflux for 4 hr
  3. customAfter completion of the reaction
  4. concentrationthe reaction mixture was concentrated under vacuum
  5. customquenched with water/ice
  6. extractionThe resulting solution was extracted with 3×200 mL of ethyl acetate
  7. washThe combined organic layers were washed with brine
  8. dry with materialdried over anhydrous sodium
  9. concentrationsulfateand concentrated under vacuum
  10. customThe residue was purified on a silica gel column with ethyl acetate/petroleum ether (1/10)

Sources & evidence

ORD record
ord-000e2322b5b14843a3580da718d959a0
Source dataset
uspto-grants-2014_04
Patent number
US08703941B2

Reaction notes

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