Acetic Acid → 2-Chloro-4-ethyl-5-fluoropyrimidine

HRID 634235ノート

反応式

HRID 634235 の反応式
[Cl:1][C:2]1[N:7]=[C:6]([C:8](C)(C(OCC)=O)[C:9](OCC)=O)[C:5]([F:20])=[CH:4][N:3]=1.CC(O)=O.Cl.O>C(Cl)Cl>[Cl:1][C:2]1[N:7]=[C:6]([CH2:8][CH3:9])[C:5]([F:20])=[CH:4][N:3]=1

参加物

6

反応物 4

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 962WaterHCID 86725111Diethyl 2-(2-chloro-5-fluoropyrimidin-4-yl)-2-methylmalonate

生成物 1

HCID 190749282-Chloro-4-ethyl-5-fluoropyrimidine収率 21%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
100 °C

実験手順

Diethyl 2-(2-chloro-5-fluoropyrimidin-4-yl)-2-methylmalonate (3.00 g, 9.85 mmol) was treated with glacial HOAc (25 mL) and 5N HCl (10 mL) and fitted with a reflux condenser and heated to 100° C. for 18 h. The reaction was cooled to RT and treated with H2O (30 mL) and DCM (45 mL) and the DCM layer separated and dried over MgSO4, filtered and concentrated. The crude residue was purified with flash chromatography (eluting with 100% DCM) affording 2-chloro-4-ethyl-5-fluoropyrimidine (328 mg, 21%) as a viscous pale yellow oil. MS (ESI, pos. ion) m/z: 161.0 (M+1). 1H NMR (400 MHz, CDCl3) δ ppm 8.34 (1H, s), 2.87 (2H, qd, J=7.6, 2.0 Hz), 1.29-1.37 (3H, t).

後処理

  1. customfitted with a reflux condenser
  2. temperatureThe reaction was cooled to RT
  3. customthe DCM layer separated
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude residue was purified with flash chromatography (eluting with 100% DCM)

出典と根拠

ORDレコード
ord-96c5fb475b344b1ba0e448a7f82a6f8b
出典データセット
uspto-grants-2016_04
特許番号
US09321756B2

反応ノート

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