Diethyl 2-(p-tolyl)malonate → HCID 178418910, compound

HRID 1358317Notes

Reaction equation

HRID 1358317 reaction equation
[C:1]1([CH3:18])[CH:6]=[CH:5][C:4]([CH:7]([C:13](OCC)=[O:14])[C:8](OCC)=[O:9])=[CH:3][CH:2]=1.C[O-].[Na+].Cl.[CH:23]([NH2:25])=[NH:24]>CO>[OH:14][C:13]1[C:7]([C:4]2[CH:5]=[CH:6][C:1]([CH3:18])=[CH:2][CH:3]=2)=[C:8]([OH:9])[N:25]=[CH:23][N:24]=1

Participants

5

Reactant 3

HCID 570878Diethyl 2-(p-tolyl)malonateHCID 10313058Methanimidamide, hydrochloride (1:1)HCID 10942334Sodium Methoxide

Product 1

HCID 178418910HCID 178418910, compoundYield 97.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

At 0° C. a solution of 14.2 g of diethyl 2-(p-tolyl)-malonate in 50 ml of methanol was slowly added to a solution of 9.4 g of sodium methylate in 300 ml of methanol. Upon completion of the addition the reaction mixture was allowed to warm up and 5.4 g of formamidine hydrochloride was added. The mixture was stirred at room temperature for 16 h. The solvent was removed under reduced pressure and the remaining residue was treated with 150 ml of 2 N hydrochloric acid. The suspension was stirred for 0.5 h. At 0-5° C., the pH was carefully adjusted to 4 using 10 N sodium hydroxide solution. The precipitate was collected, washed with cold water, isopropanol, and diethyl ether and dried under high vacuum at 65° C. to give 11.2 g of 4,6-dihydroxy-5-(p-tolyl)-pyrimidine (or a tautomer) as a white powder.

Workup

  1. additionUpon completion of the addition the reaction mixture
  2. temperatureto warm up
  3. customThe solvent was removed under reduced pressure
  4. additionthe remaining residue was treated with 150 ml of 2 N hydrochloric acid
  5. stirringThe suspension was stirred for 0.5 h
  6. customAt 0-5° C.
  7. customThe precipitate was collected
  8. washwashed with cold water, isopropanol, and diethyl ether
  9. customdried under high vacuum at 65° C.

Sources & evidence

ORD record
ord-c0732e60f8dc44e4929cdd71d6a3e3dd
Source dataset
uspto-grants-2003_07
Patent number
US06596719B1

Reaction notes

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