Formamidine acetate → Ethyl 4,6-dimethylpyrimidine-5-carboxylate

HRID 2244892Notes

Reaction equation

HRID 2244892 reaction equation
[C:1]([C:4](=[C:10](OCC)[CH3:11])[C:5]([O:7][CH2:8][CH3:9])=[O:6])(=O)[CH3:2].C(O)(=O)C.[CH:19]([NH2:21])=[NH:20].[O-]CC.[Na+]>C(O)C>[CH3:2][C:1]1[C:4]([C:5]([O:7][CH2:8][CH3:9])=[O:6])=[C:10]([CH3:11])[N:21]=[CH:19][N:20]=1

Participants

5

Reactant 3

HCID 160693Formamidine acetateHCID 231474ethyl 2-acetyl-3-ethoxybut-2-enoateHCID 2723922Sodium ethoxide

Product 1

HCID 20619427Ethyl 4,6-dimethylpyrimidine-5-carboxylateYield 76.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
90 °C

Procedure

Ethyl 2-acetyl-3-ethoxybut-2-enoate (10.7 g, 0.0537 mol), formamidine acetate (5.6 g, 0.054 mol) and sodium ethoxide (2.7 M in ethanol, 20.0 mL) were mixed in ethanol (30 mL) and the mixture was stirred at 90° C. for 4 h. The reaction mixture was cooled, quenched with water and concentrated. The crude material was purified by flash chromatography on silical gel, eluting with 10%, 50% ethyl acetate/hexane to afford the desired product (7.4 g, 76%) as a yellow oil. MS (EI) 181.1 (M+1). 1H NMR (300 MHz, CDCl3) δ (ppm) 8.97 (s, 1H), 4.44 (q, 2H), 2.56 (s, 6H), 1.42 (t, 3H).

Workup

  1. temperatureThe reaction mixture was cooled
  2. customquenched with water
  3. concentrationconcentrated
  4. customThe crude material was purified by flash chromatography on silical gel
  5. washeluting with 10%, 50% ethyl acetate/hexane

Sources & evidence

ORD record
ord-3b21a43bae5744f79339b4e06a35f436
Source dataset
uspto-grants-2010_03
Patent number
US07678798B2

Reaction notes

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