Pyridine → 4-Chloro(1)benzothieno(3,2-d)pyrimidine

HRID 634539Notes

Reaction equation

HRID 634539 reaction equation
[N:1]1[C:6]2[C:7]3[CH:13]=[CH:12][CH:11]=[CH:10][C:8]=3[S:9][C:5]=2[C:4](=O)[NH:3][CH:2]=1.N1C=CC=CC=1.P(Cl)(Cl)([Cl:23])=O>>[Cl:23][C:4]1[C:5]2[S:9][C:8]3[CH:10]=[CH:11][CH:12]=[CH:13][C:7]=3[C:6]=2[N:1]=[CH:2][N:3]=1

Participants

4

Reactant 3

HCID 1049PyridineHCID 24813Phosphorus oxychlorideHCID 135442517[1]benzothieno[3,2-d]pyrimidin-4(3H)-one

Product 1

HCID 8218354-Chloro(1)benzothieno(3,2-d)pyrimidineYield 169.7%

Conditions

Temperature
110 °C

Procedure

Benzo[4,5]thieno[3,2-d]pyrimidin-4(3H)-one (10.78 g, 26.7 mmol) was treated with pyridine (2.68 mL, 33.3 mmol) and phosphoryl trichloride (53.4 mL, 573 mmol), then heated to reflux at 110° C. for 1 hr. Excess POC3 was removed and cautiously quenched with ice water in an ice bath. The pH was adjusted to ˜5 with ammonium hydroxide. Solid was collected by filtration washed with water. The solid was dried to give 4-chlorobenzo[4,5]thieno[3,2-d]pyrimidine (10 g, 85% yield).

Workup

  1. temperatureheated
  2. customExcess POC3 was removed
  3. customcautiously quenched with ice water in an ice bath
  4. filtrationSolid was collected by filtration
  5. washwashed with water
  6. customThe solid was dried

Sources & evidence

ORD record
ord-4aeaefb447f3446780396f3ac5032d94
Source dataset
uspto-grants-2016_04
Patent number
US09324949B2

Reaction notes

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