Hydrochloric Acid → Diethyl pyrimidine-2,4-dicarboxylate

HRID 1469672Notes

Reaction equation

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]

Participants

Conditions

Temperature: 60 °C

Procedure

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.

Workup

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

Sources & evidence

ORD record: ord-51e659cac013460ca1d52cdeb76ed34b
Source dataset: uspto-grants-2015_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09006249B2

Reaction notes

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