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

HRID 10242Notes

Reaction equation

HRID 10242 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-5f2fb7b342c44f879faf621a08f0c6ed
Source dataset
uspto-grants-2006_08
Patent number
US07094781B2

Reaction notes

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