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

HRID 8591Notes

Reaction equation

HRID 8591 reaction equation
C[O-].[Na+].C([O:6][C:7](=O)[CH:8]([C:14]1[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][CH:15]=1)[C:9](OCC)=[O:10])C.Cl.[CH:23]([NH2:25])=[NH:24]>CO>[C:17]1([CH3:20])[CH:18]=[CH:19][C:14]([C:8]2[C:9]([OH:10])=[N:24][CH:23]=[N:25][C:7]=2[OH:6])=[CH:15][CH:16]=1

Participants

5

Reactant 3

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

Product 1

HCID 178418910HCID 178418910, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

Sodium methylate (17 g) was dissolved in methanol (600 ml) at 0° C. 2-p-tolyl-malonic acid diethyl ester (24.5 ml, commercially available from Aldrich), dissolved in 150 ml methanol, was added within 30 min. Stirring was continued for 1 h while slowly warming the mixture to rt. Formamidine hydrochloride (9.9 g, commercially available from Fluka) was added and stirring was continued for 16 h. The solvent was evaporated and 2 M hydrochloric acid (200 ml) was added to the residue followed by slow addition of 10 M sodium hydroxide to adjust the pH to 5. The precipitated product was filtered off and washed subsequently with water and diethylether and dried to give 5-p-tolyl-pyrimidine-4,6-diol (17.7 g). 1H-NMR (300 MHz, d6-DMSO): 8.0(s, 1H); 7.4(d, 2H); 7.1(d, 2H); 2.25(s, 3H).

Workup

  1. additionwas added within 30 min
  2. stirringstirring
  3. waitwas continued for 16 h
  4. customThe solvent was evaporated
  5. addition2 M hydrochloric acid (200 ml) was added to the residue
  6. additionfollowed by slow addition of 10 M sodium hydroxide
  7. filtrationThe precipitated product was filtered off
  8. washwashed subsequently with water and diethylether
  9. customdried

Sources & evidence

ORD record
ord-054b7a2c02c6492294fcf260040320fc
Source dataset
uspto-grants-2006_08
Patent number
US07091201B2

Reaction notes

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