Phosphorus oxychloride → HCID 23726818, compound

HRID 910198Notes

Reaction equation

HRID 910198 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>ClCCl>[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

4

Reactant 2

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

Product 1

HCID 23726818HCID 23726818, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A stirred suspension of 2-chloromethyl-5-phenyl-3H-thieno[2,3-d]pyrimidin-4-one (1.5 g, 5.42 mmol) and phosphoryl chloride (23 ml) was heated under reflux for 7 hours and then left to stand at ambient temperature for 18 hours. The excess phosphoryl chloride was removed in vacuo to give a dark residue, which was dissolved in dichloromethane (100 ml) and then washed with water (2×100 ml) followed by saturated sodium hydrogen carbonate solution (100 ml). The organic extract was dried (MgSO4) and the solvent was removed in vacuo to give the crude product. Purification by flash chromatography (silica) eluting with dichloromethane gave 4-chloro-2-chloromethyl-5-phenylthieno[2,3-d]pyrimidine as a pale-yellow solid (1.42 g).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 7 hours
  3. waitleft
  4. customThe excess phosphoryl chloride was removed in vacuo
  5. customto give a dark residue, which
  6. washwashed with water (2×100 ml)
  7. extractionThe organic extract
  8. dry with materialwas dried (MgSO4)
  9. customthe solvent was removed in vacuo
  10. customto give the crude product
  11. customPurification by flash chromatography (silica)
  12. washeluting with dichloromethane

Sources & evidence

ORD record
ord-7128eea9862b4c6e968acf49ab205c33
Source dataset
uspto-grants-2011_09
Patent number
US08022076B2

Reaction notes

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