1,3-Dimethyl 2-(4-chlorophenyl)propanedioate → 5-(4-Chlorophenyl)pyrimidine-4,6-diol

HRID 965628

Reaction equation

HRID 965628 reaction equation
C[O:2][C:3](=O)[CH:4]([C:9]1[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][CH:10]=1)[C:5](OC)=[O:6].C[O-].[Na+].Cl.[CH:21]([NH2:23])=[NH:22]>CO>[Cl:15][C:12]1[CH:13]=[CH:14][C:9]([C:4]2[C:5]([OH:6])=[N:22][CH:21]=[N:23][C:3]=2[OH:2])=[CH:10][CH:11]=1

Participants

5

Reactant 3

HCID 27851471,3-Dimethyl 2-(4-chlorophenyl)propanedioateHCID 10313058Methanimidamide, hydrochloride (1:1)HCID 10942334Sodium Methoxide

Product 1

HCID 1784188705-(4-Chlorophenyl)pyrimidine-4,6-diolYield 94.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A solution of 18.90 g of 2-(4-chloro-phenyl)-malonic acid dimethyl ester in 200 ml of methanol was added dropwise at 0° C. to a solution of 14.60 g sodium methylate in 150 ml of methanol. The mixture was stirred for 1 h at 0° C. before 7.66 g of formamidine hydrochloride was added. The suspension was stirred at rt for 20 h. The solvent was removed and the residue was suspended in 200 ml 2 N aq. HCl. The pH of the suspension was carfully adjusted to 4-5 by adding 20 ml of 10 M NaOH, stirring was continued for 30 min. The white precipitate was collected, washed with water and diethyl ether and dried to give 16.44 g of 5-(4-chlorophenyl)-pyrimidine-4,6-diol as a white powder. LC-MS: tR=2.75 min, [M+H]+=222.96 (ES+), [M−H]−=220.92 (ES−).

Workup

  1. additionwas added
  2. customThe solvent was removed
  3. additionby adding 20 ml of 10 M NaOH
  4. stirringstirring
  5. waitwas continued for 30 min
  6. customThe white precipitate was collected
  7. washwashed with water and diethyl ether
  8. customdried

Sources & evidence

ORD record
ord-b5becde1c20240bbbc3691efa853b356
Source dataset
uspto-grants-2005_10
Patent number
US06951856B2

Linked notes

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