Diethyl (ethoxymethylene)malonate → HCID 178469768, compound

HRID 599315Notes

Reaction equation

HRID 599315 reaction equation
[CH3:1][C:2]([C:5]([NH2:7])=[NH:6])([CH3:4])[CH3:3].Cl.[O-]CC.[Na+].C([O:15][CH:16]=[C:17]([C:23](OCC)=O)[C:18]([O:20][CH2:21][CH3:22])=[O:19])C>C(O)C>[C:2]([C:5]1[N:7]=[C:16]([OH:15])[C:17]([C:18]([O:20][CH2:21][CH3:22])=[O:19])=[CH:23][N:6]=1)([CH3:4])([CH3:3])[CH3:1]

Participants

5

Reactant 3

HCID 6871Diethyl (ethoxymethylene)malonateHCID 2723922Sodium ethoxideHCID 2781880Propanimidamide, 2,2-dimethyl-, hydrochloride (1:1)

Product 1

HCID 178469768HCID 178469768, compoundYield 36%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

In ethanol (40 mL) was placed t-butylcarbamidine hydrochloride (3.71 g, 27.2 mmol). This was treated with 21% sodium ethoxide in ethanol (8.80 g, 27.2 mmol) and stirred at RT for 15 min. To this was added the diethyl ethoxymethylenemalonate (5.87 g, 27.2 mmol) and the reaction mixture was stirred overnight at RT. The reaction mixture was refluxed for 1 hour and then cooled to RT. The solution was evaporated and the residue was dissolved in water (100 mL) and the pH adjusted to 3-4 (wet litmus) with acetic acid. The mixture formed a precipitate. The solid collected by filtration, washed with water (50 mL) and dried under vacuum to obtain ethyl 2-tert-butyl-4-hydroxypyrimidine-5-carboxylate (2.18 g, 36% yield). 1H NMR (400 MHz, DMSO-d6): δ 12.6 (brs, 1H), 8.44 (s, 1H), 4.20 (q, J=7.2 Hz, 2H), 1.25 (s, 9H), 1.23 (t, J=7.2 Hz, 3H); MS (ESI) m/z: 225.0 (M+H+).

Workup

  1. stirringthe reaction mixture was stirred overnight at RT
  2. temperatureThe reaction mixture was refluxed for 1 hour
  3. temperaturecooled to RT
  4. customThe solution was evaporated
  5. dissolutionthe residue was dissolved in water (100 mL)
  6. customThe mixture formed a precipitate
  7. filtrationThe solid collected by filtration
  8. washwashed with water (50 mL)
  9. customdried under vacuum

Sources & evidence

ORD record
ord-ed04c57829a5467eb7e3f14200f81875
Source dataset
uspto-grants-2011_03
Patent number
US07897762B2

Reaction notes

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