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

反応式

[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

参加物

反応物 3

HCID 11130Triethylamine hydrochloride

HCID 24813Phosphorus oxychloride

HCID 2871105-Phenyluracil

生成物 1

HCID 123565972,4-Dichloro-5-phenylpyrimidine収率 100%

実験手順

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) δ8.49 (1H, s), 7.45 (3H, m), 7.35 (2H, m).