Triethylamine hydrochloride → 2,4-Dichloro-5-phenylpyrimidine

HRID 1176033Notes

Reaction equation

HRID 1176033 reaction equation
[C:1]1([C:7]2[C:8](=O)[NH:9][C:10](=O)[NH:11][CH:12]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[ClH:15].C(N(CC)CC)C.O=P(Cl)(Cl)[Cl:25]>>[Cl:15][C:10]1[N:9]=[C:8]([Cl:25])[C:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)=[CH:12][N:11]=1

Participants

4

Reactant 3

HCID 11130Triethylamine hydrochlorideHCID 24813Phosphorus oxychlorideHCID 2871105-Phenyluracil

Product 1

HCID 123565972,4-Dichloro-5-phenylpyrimidineYield 100%

Procedure

To 5-Phenyl-1H-pyrimidine-2,4-dione (110 mg, 0.585 mmol) and triethyl amine hydrochloride (317 mg, 2.3 mmol) was added POCl3 (15 mL) and the solution was heated to 120 C for 72 h. POCl3 was removed in vacuum and the resulting brown oil was quenched with ice water and treated with saturated NaHCO3, extracted with ethyl acetate, washed with brine, dried (Na2SO4) to give 2,4-Dichloro-5-phenyl-pyrimidine 131 mg (100% yield). HPLC tr=7.09 min (100%), FIA-MS 224.9 (M+H), HNMR (500 MHz, CDCl3) 8.49 (1H, s), 7.45 (3H, m), 7.35 (2H, m).

Workup

  1. temperaturethe solution was heated to 120 C for 72 h
  2. customPOCl3 was removed in vacuum
  3. customthe resulting brown oil was quenched with ice water
  4. additiontreated with saturated NaHCO3
  5. extractionextracted with ethyl acetate
  6. washwashed with brine
  7. dry with materialdried (Na2SO4)

Sources & evidence

ORD record
ord-883b35b8669b4d9597e9c1296fff4e56
Source dataset
uspto-grants-2010_11
Patent number
US07842712B2

Reaction notes

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