Phosphorus oxychloride → 4-Chlorothieno[2,3-d]pyrimidine

HRID 335254Notes

Reaction equation

HRID 335254 reaction equation
[N:1]1[C:6]2[S:7][CH:8]=[CH:9][C:5]=2[C:4](=O)[NH:3][CH:2]=1.P(Cl)(Cl)([Cl:13])=O>ClCCCl>[Cl:13][C:4]1[C:5]2[CH:9]=[CH:8][S:7][C:6]=2[N:1]=[CH:2][N:3]=1

Participants

4

Reactant 2

HCID 24813Phosphorus oxychloride2×HCID 2808547thieno(2,3-d)pyrimidin-4(3H)-one

Product 1

HCID 7366184-Chlorothieno[2,3-d]pyrimidineYield 29%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Conditions

Temperature
90 °C

Procedure

Thieno[2,3-d]pyrimidin-4(3H)-one (1.2 g, 7.9 mmol) was diluted in 1,2-dichloroethane (10 mL). Phosphorous oxychloride (1.4 mL, 15.7 mmol) was added. The reaction was stirred at 90° C. for 16 hours. An additional equivalent of phosphorous oxychloride (0.7 mL, 7.9 mmol) was added and the solution continued stirring for 4 hours. The solution was cooled, concentrated, and neutralized with saturated NaHCO3 solution. The material was extracted with a chloroform:isopropyl alcohol mixture and the organic layer was separated and concentrated. Flash chromatography gave the title compound (0.39 g, 29%).

Workup

  1. stirringthe solution continued stirring for 4 hours
  2. temperatureThe solution was cooled
  3. concentrationconcentrated
  4. extractionThe material was extracted with a chloroform
  5. customisopropyl alcohol mixture and the organic layer was separated
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-2e86e1f9f3ad457cb32e13827168192e
Source dataset
uspto-grants-2014_11
Patent number
US08883828B2

Reaction notes

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