Hydrochloric Acid → Diethyl pyrimidine-2,4-dicarboxylate

HRID 1469672ノート

反応式

HRID 1469672 の反応式
N(OC(C)(C)C)=O.N[C:9]1[N:14]=[C:13]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[N:12]=[C:11]([C:20]([O:22][CH2:23][CH3:24])=[O:21])[CH:10]=1.Cl>CN(C=O)C>[N:14]1[CH:9]=[CH:10][C:11]([C:20]([O:22][CH2:23][CH3:24])=[O:21])=[N:12][C:13]=1[C:15]([O:17][CH2:18][CH3:19])=[O:16]

参加物

5

反応物 3

HCID 313Hydrochloric AcidHCID 10906Tert-Butyl nitriteHCID 10857553Diethyl 6-aminopyrimidine-2,4-dicarboxylate

生成物 1

HCID 66701935Diethyl pyrimidine-2,4-dicarboxylate

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒2 回

反応条件

温度
60 °C

実験手順

Next, To a stirred solution of tert-butyl nitrite (268 mg, 2.34 mmol.) in DMF (5 mL) at 60° C. is added a solution of diethyl 6-aminopyrimidine-2,4-dicarboxylate (280 mg, 1.17 mmol) in DMF (0.5 mL) dropwise and mixture is heated at 60° C. for 18 hours. The mixture is cooled to room temperature and poured into 1N HCl (10 mL). The mixture is extracted three times with ethyl acetate and the combined organic layers are washed with water and brine then is dried over magnesium sulfate. The solvent is removed under reduced pressure and the residue is purified by flash chromatography (heptane/ethyl acetate=4:1) to give diethyl pyrimidine-2,4-dicarboxylate.

後処理

  1. temperatureThe mixture is cooled to room temperature
  2. extractionThe mixture is extracted three times with ethyl acetate
  3. washthe combined organic layers are washed with water and brine
  4. dry with materialthen is dried over magnesium sulfate
  5. customThe solvent is removed under reduced pressure
  6. customthe residue is purified by flash chromatography (heptane/ethyl acetate=4:1)

出典と根拠

ORDレコード
ord-51e659cac013460ca1d52cdeb76ed34b
出典データセット
uspto-grants-2015_04
特許番号
US09006249B2

反応ノート

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