Nitric Acid → Ethyl 4-(2-fluorophenyl)-1,2-dihydro-6-methyl-2-oxopyrimidine-5-carboxylate

HRID 1036620Notes

Reaction equation

HRID 1036620 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]1[C:13]([C:14]([O:16][CH2:17][CH3:18])=[O:15])=[C:12]([CH3:19])[NH:11][C:10](=[O:20])[NH:9]1.[N+]([O-])(O)=O.[OH-].[Na+]>>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:13]([C:14]([O:16][CH2:17][CH3:18])=[O:15])=[C:12]([CH3:19])[NH:11][C:10](=[O:20])[N:9]=1

Participants

4

Reactant 3

HCID 944Nitric AcidHCID 14798Sodium HydroxideHCID 2831294Ethyl 4-(2-fluorophenyl)-6-methyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate

Product 1

HCID 59421129Ethyl 4-(2-fluorophenyl)-1,2-dihydro-6-methyl-2-oxopyrimidine-5-carboxylateYield 76%

Procedure

Ethyl 4-(2-fluorophenyl)-1,2,3,4-tetrahydro-6-methyl-2-oxopyrimidine-5-carboxylate (2.00 g, 7.2 mmol) was added in small portions to a stirred solution of a 60% nitric acid solution (12 mL) at 0° C. over 5 min. The resulting solution was warmed to room temperature (30 min) and then poured into ice and basified slowly with 6N NaOH. The product was extracted with CHCl3 (3×50 mL), dried, and concentrated. The residue was purified by Biotage SP1 on packed silica gel column (7%-20% MeOH/CH2Cl2 gradient) to give ethyl 4-(2-fluorophenyl)-1,2-dihydro-6-methyl-2-oxopyrimidine-5-carboxylate as a green foam (1.5 g, 76%). Mass Spec. LCMS 277 (M+1).

Workup

  1. extractionThe product was extracted with CHCl3 (3×50 mL)
  2. customdried
  3. concentrationconcentrated
  4. customThe residue was purified by Biotage SP1

Sources & evidence

ORD record
ord-bd280e8c630a458fa4f738c0a291d807
Source dataset
uspto-grants-2013_10
Patent number
US08546414B2

Reaction notes

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