Phosphorus oxychloride → HCID 23726818, compound

HRID 928607Notes

Reaction equation

HRID 928607 reaction equation
[Cl:1][CH2:2][C:3]1[NH:4][C:5](=O)[C:6]2[C:11]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)=[CH:10][S:9][C:7]=2[N:8]=1.P(Cl)(Cl)([Cl:21])=O>>[Cl:21][C:5]1[C:6]2[C:11]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)=[CH:10][S:9][C:7]=2[N:8]=[C:3]([CH2:2][Cl:1])[N:4]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 23741772-Chloromethyl-5-phenyl-3H-thieno[2,3-d]pyrimidin-4-one

Product 1

HCID 23726818HCID 23726818, compound

Conditions

Temperature
105 °C

Procedure

A suspension of 2-(chloromethyl)-5-phenyl-3H-thieno[2,3-d]pyrimidin-4-one (1.50 g, ex Enamine) in phosphorus oxychloride (23 mL) was heated to reflux (105° C.) overnight. The reaction was cooled and the solvent was evaporated. Toluene (30 mL) was added and the mixture was evaporated again. The residue was dissolved in dichloromethane (100 mL). It was washed with water (1×100 mL) and saturated aqueous sodium bicarbonate solution (1×100 mL), dried (sodium sulfate), filtered and evaporated to give the target compound as a yellow solid (1.45 g). m/z [M+H]+ 294.8/296.8. Retention time 4.99 min (LCMS method+ve 6 min). It was used in the next step without further purification.

Workup

  1. temperaturewas heated
  2. temperatureThe reaction was cooled
  3. customthe solvent was evaporated
  4. additionToluene (30 mL) was added
  5. customthe mixture was evaporated again
  6. dissolutionThe residue was dissolved in dichloromethane (100 mL)
  7. washIt was washed with water (1×100 mL) and saturated aqueous sodium bicarbonate solution (1×100 mL)
  8. dry with materialdried (sodium sulfate)
  9. filtrationfiltered
  10. customevaporated

Sources & evidence

ORD record
ord-83d578e0632e49a7bbd35fd26533a99f
Source dataset
uspto-grants-2016_03
Patent number
US09290511B2

Reaction notes

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