2,4,6-Triethyl 1,3,5-triazine-2,4,6-tricarboxylate → Diethyl 6-aminopyrimidine-2,4-dicarboxylate

HRID 1469671Notes

Reaction equation

[N:1]1[C:6]([C:7]([O:9][CH2:10][CH3:11])=[O:8])=[N:5][C:4]([C:12]([O:14][CH2:15][CH3:16])=[O:13])=[N:3][C:2]=1[C:17](OCC)=O.[Cl-].NC(=[NH2+])C>CN(C=O)C>[NH2:1][C:2]1[N:3]=[C:4]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[N:5]=[C:6]([C:7]([O:9][CH2:10][CH3:11])=[O:8])[CH:17]=1

Participants

Conditions

Temperature: 100 °C

Procedure

To a stirred solution of triethyl 1,3,5-triazine-2,4,6-tricarboxylate (J. Org. Chem. 59, 4950, 1994) (2.02 g, 6.80 mmol.) in DMF (15 mL) is added 1-aminoethaniminium chloride (1.29 g, 13.60 mmol). After the addition, the mixture is heated at 100° C. for 18 hours then the mixture is extracted three times with ethyl acetate. 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=3:1) to give diethyl 6-aminopyrimidine-2,4-dicarboxylate; HPLC Retention time 0.89 minutes (condition C); MS 240.3 (M+1).

Workup

additionAfter the addition
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=3:1)

Sources & evidence

ORD record: ord-09a0681d16464b9dacd873f7cde1e0de
Source dataset: uspto-grants-2015_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09006249B2

Reaction notes

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