2-Methyl-2-thiopseudourea → HCID 178418871, 화합물

HRID 1696436

반응식

HRID 1696436 반응식
[CH2:1]([O:3][C:4](=[O:15])[C:5](=[CH:11][O:12]CC)[C:6](OCC)=O)[CH3:2].[CH3:16][S:17][C:18](=[NH:20])[NH2:19].CC[O-].[Na+]>CCO>[CH2:1]([O:3][C:4]([C:5]1[C:11]([OH:12])=[N:19][C:18]([S:17][CH3:16])=[N:20][CH:6]=1)=[O:15])[CH3:2]

참가 물질

5

반응물 3

HCID 51422-Methyl-2-thiopseudoureaHCID 6871Diethyl (ethoxymethylene)malonateHCID 2723922Sodium ethoxide

생성물 1

HCID 178418871HCID 178418871, 화합물수율 158.1%

시약·촉매·용매 1

HCID 702Ethanol용매

반응 조건

온도
5 °C

실험 절차

To a solution of 2-ethoxymethylenemalonic acid diethyl ester (59.0 g, 273 mmol) in EtOH (300 mL) was added 2-methyl-isothiourea (41.5 g, 150 mmol) in an ice-H2O bath. An EtOHic solution of EtONa (2M, 300 mL) was added dropwise maintaining the reaction temperature under 5° C. The mixture was warmed to RT and stirred for 3 h. After standing overnight, the solvent was removed under reduced pressureand the residue was dissolved in H2O (800 mL) at 0° C. The solution was acidified to pH 3 with conc. HCl and the precipitate collected by filtration and air-dried to yield 4-hydroxy-2-methylsulfanyl-pyrimidine-5-carboxylic acid ethyl ester as a white solid (50.8 g, 87.6% yield). 1H NMR (400 MHz, DMSO-d6): δ 8.48 (s, 1H), 4.20 (q, J=9.6 Hz, 2H), 2.51 (s, 3H), 1.23 (t, J=9.6 Hz, 3H).

후처리

  1. temperatureThe mixture was warmed to RT
  2. waitAfter standing overnight
  3. customthe solvent was removed
  4. dissolutionwas dissolved in H2O (800 mL) at 0° C
  5. filtrationthe precipitate collected by filtration
  6. customair-dried

출처 및 근거

ORD 기록
ord-fd915514089444d8a0eae3c0f5d8585e
출처 데이터셋
uspto-grants-2012_04
특허 번호
US08163756B2

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