Ethyl Acetate → HCID 54721883, compound

HRID 1375546Notes

Reaction equation

HRID 1375546 reaction equation
CC(C)(C)C([O:5][C:6]1[C:11](=[O:12])[N:10]([CH3:13])[C:9]([C:14]([O:16][CH2:17][CH3:18])=[O:15])=[N:8][C:7]=1[C:19]([O:21]C)=O)=O.OC1C(O)=C(C(OC)=O)N=C(C(O)=O)N=1.[F:40][C:41]1[CH:48]=[CH:47][C:44]([CH2:45][NH2:46])=[CH:43][CH:42]=1.CCOC(C)=O>CN(C=O)C>[F:40][C:41]1[CH:48]=[CH:47][C:44]([CH2:45][NH:46][C:19]([C:7]2[N:8]=[C:9]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[N:10]([CH3:13])[C:11](=[O:12])[C:6]=2[OH:5])=[O:21])=[CH:43][CH:42]=1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 673264-FluorobenzylamineHCID 86596288HCID 86596288, compoundHCID 178499103HCID 178499103, compound

Product 1

HCID 54721883HCID 54721883, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

2-Ethyl 4-methyl 5-[(2,2-dimethylpropanoyl)oxy]-1-methyl-6-oxo-1,6-dihydropyrimidine-2,4-dicarboxylate (made by protection and alkylation of the starting material of Example 4, Step 1 using procedures similar to those set forth in Examples 1 or 2) was dissolved in DMF, 4-fluorobenzylamine (3.1 eq.) was added and the mixture was stirred at 90° C. overnight. After concentration of the solvent, the residue was taken into EtOAc, washed with 1 N HCl, dried over Na2SO4 and evaporated to obtain crude N-(4-fluorobenzyl)-2-ethoxycarbonyl-1-methyl-5-hydroxy-6-oxo-1,6-dihydropyrimidine-4-carboxamide. To this crude product was added 2-picolylamine (8 eq.), and the reaction was stirred at 90° C. overnight. The title product was obtained as its trifluoroacetic salt by preparative RP-HPLC purification (C18 gradient of CH3CN/H2O+0.01% TFA).

Workup

  1. washwashed with 1 N HCl
  2. dry with materialdried over Na2SO4
  3. customevaporated

Sources & evidence

ORD record
ord-046335215af94cb5b2d414f33ff34b00
Source dataset
uspto-grants-2007_01
Patent number
US07169780B2

Reaction notes

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