Dimethyl methoxymethylenemalonate → HCID 178498799, compound

HRID 1696574Notes

Reaction equation

HRID 1696574 reaction equation
Cl.[C:2]([NH2:8])(=[NH:7])[C:3]([CH3:6])([CH3:5])[CH3:4].C[O-].[Na+].C[O:13][CH:14]=[C:15]([C:20](OC)=O)[C:16]([O:18][CH3:19])=[O:17]>CO>[C:3]([C:2]1[N:8]=[C:14]([OH:13])[C:15]([C:16]([O:18][CH3:19])=[O:17])=[CH:20][N:7]=1)([CH3:6])([CH3:5])[CH3:4]

Participants

5

Reactant 3

HCID 90770Dimethyl methoxymethylenemalonateHCID 2781880Propanimidamide, 2,2-dimethyl-, hydrochloride (1:1)HCID 10942334Sodium Methoxide

Product 1

HCID 178498799HCID 178498799, compoundYield 45%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Pivalamidine hydrochloride (5.00 g, 37 mmol) dissolved in methanol (80 mL) was treated with NaOMe (2.0 g, 37 mmol) and stirred at RT for 15 min. To this was added dimethyl 2-(methoxymethylene)malonate (6.4 g, 37 mmol) and the solution stirred at RT overnight. The solution was heated at reflux for 1 h, then cooled to RT and concentrated. The oily mass was dissolved in H2O (125 mL) and the pH adjusted to ˜3 (wet litmus) with AcOH. The precipitated solids were collected by filtration, washed with H2O (50 mL) and dried to yield methyl 2-t-butyl-4-hydroxypyrimidine-5-carboxylate (3.50 g, 45%). 1H NMR (400 MHz, DMSO-d6): δ 1.29 (s, 9H), 2.97 (s, 3H), 8.47 (s, 1H).

Workup

  1. stirringthe solution stirred at RT overnight
  2. temperatureThe solution was heated
  3. temperatureat reflux for 1 h
  4. temperaturecooled to RT
  5. concentrationconcentrated
  6. dissolutionThe oily mass was dissolved in H2O (125 mL)
  7. filtrationThe precipitated solids were collected by filtration
  8. washwashed with H2O (50 mL)
  9. customdried

Sources & evidence

ORD record
ord-c2482fc2f3344fb3a01beff320a8bb33
Source dataset
uspto-grants-2012_04
Patent number
US08163756B2

Reaction notes

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