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

HRID 2384094Notes

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-87571b361d4b4fc78acce1272bd78cdb
Source dataset: uspto-grants-2012_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08263629B2

Reaction notes

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