Phosphorus oxychloride → 4-Chloro-2,6-diphenylpyrimidine

HRID 269753Notes

Reaction equation

HRID 269753 reaction equation
P(Cl)(Cl)(Cl)=O.[C:6]1([C:12]2[NH:17][C:16](=O)[CH:15]=[C:14]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[N:13]=2)[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.P(Cl)(Cl)(Cl)(Cl)[Cl:26]>>[Cl:26][C:16]1[CH:15]=[C:14]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[N:13]=[C:12]([C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=2)[N:17]=1

Participants

4

Reactant 3

HCID 24813Phosphorus oxychlorideHCID 24819Phosphorus pentachlorideHCID 1354755602,6-Diphenylpyrimidin-4-ol

Product 1

HCID 5820414-Chloro-2,6-diphenylpyrimidineYield 65%

Procedure

Phosphorous oxychloride (9.30 mL, 99.8 mmol, 7.5 eq.) was added dropwise to 2,6-diphenyl-3H-pyrimidin-4-one (10) (3.3 g, 13.3 mmol) in a vigorous reaction. To this mixture was added slowly phosphorous pentachloride (2.77 g, 13.3 mmol, 1 eq.) and the reaction mixture was stirred at reflux for 3 hours. The reaction mixture was then quenched by pouring into ice-water, and extracted with ethyl acetate (3×150 mL). The combined organic layers were washed with water and brine, dried (MgSO4) and then concentrated to give a yellow solid. This was recrystallised from hot ethanol to give fine white needles (65%). 1H NMR δ (CDCl3): 8.60-8.18 (m, 5H, Ar), 7.63 (s, 1H, Ar), 7.51-7.57 (m, 5H, Ar).

Workup

  1. temperatureat reflux for 3 hours
  2. customThe reaction mixture was then quenched
  3. additionby pouring into ice-water
  4. extractionextracted with ethyl acetate (3×150 mL)
  5. washThe combined organic layers were washed with water and brine
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated
  8. customto give a yellow solid
  9. customThis was recrystallised from hot ethanol

Sources & evidence

ORD record
ord-e742a79bbea44d05b32f42ec2943b17f
Source dataset
uspto-grants-2008_11
Patent number
US07449470B2

Reaction notes

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