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

HRID 1181224Notes

Reaction equation

HRID 1181224 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 diethyl 2-(p-tolyl)-malonate (14.2 g) in methanol (50 ml) was slowly added to a solution of sodium methylate (9.4 g) in methanol (300 ml). Upon completion of the addition the reaction mixture was allowed to warm up and formamidine hydrochloride (5.4 g) was added. The mixture was stirred at r.t. for 16 h. The solvent was removed under reduced pressure and the remaining residue was treated with 2 N hydrochloric acid (150 ml). 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 4,6-dihydroxy-5-(p-tolyl)-pyrimidine (11.2 g) (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 2 N hydrochloric acid (150 ml)
  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-bd2a636e389a4ae0918a5345eb717a85
Source dataset
uspto-grants-2007_10
Patent number
US07285549B2

Reaction notes

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