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

HRID 8611

반응식

HRID 8611 반응식
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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 887Methanol용매2회

실험 절차

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

후처리

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

출처 및 근거

ORD 기록
ord-b4421387e1174e2989ff360b17023739
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07091201B2

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