Methyl formate → Methyl 3-(4-oxo-2-thioxo-1,2,3,4-tetrahydro-5-pyrimidinyl)propanoate

HRID 474610

반응식

HRID 474610 반응식
CC(C)([O-])C.[K+].[C:7]([O:16][CH3:17])(=[O:15])[CH2:8][CH2:9][CH2:10][C:11]([O:13]C)=O.[CH:18](OC)=O.[NH2:22][C:23]([NH2:25])=[S:24]>C(OC)(C)(C)C.CO>[O:13]=[C:11]1[C:10]([CH2:9][CH2:8][C:7]([O:16][CH3:17])=[O:15])=[CH:18][NH:25][C:23](=[S:24])[NH:22]1

참가 물질

7

반응물 4

HCID 7865Methyl formateHCID 14242Dimethyl GlutarateHCID 2723790ThioureaHCID 23665647Potassium tert-butoxide

생성물 1

HCID 86666200Methyl 3-(4-oxo-2-thioxo-1,2,3,4-tetrahydro-5-pyrimidinyl)propanoate수율 30.2%

시약·촉매·용매 2

HCID 887Methanol용매HCID 15413tert-Butyl methyl ether용매2회

실험 절차

To a suspension of potassium tert-butoxide (7.29 g, 64.9 mmol) in t-butylmethyl ether (100 mL) was added a solution of dimethyl pentanedioate (5.2 g, 32.5 mmol) and methyl formate (1.950 g, 32.5 mmol) in t-butylmethyl ether (50 mL). The mixture was stirred overnight and concentrated to dryness afford the yellow oil. The oil was dissolved in methanol (80 mL), to which thiourea (2.72 g, 35.7 mmol) was added. The mixture was heated to reflux overnight. The result mixture was concentrated and dissolved in water, adjust pH to 3 with AcOH. The solution was extracted with DCM three times. The combined organic layers were dried over Na2SO4, filtered and concentrated to afford the title compound (2.1 g, 9.80 mmol, 30.2% yield).

후처리

  1. concentrationconcentrated to dryness
  2. customafford the yellow oil
  3. additionwas added
  4. temperatureThe mixture was heated
  5. temperatureto reflux overnight
  6. concentrationThe result mixture was concentrated
  7. dissolutiondissolved in water
  8. extractionThe solution was extracted with DCM three times
  9. dry with materialThe combined organic layers were dried over Na2SO4
  10. filtrationfiltered
  11. concentrationconcentrated

출처 및 근거

ORD 기록
ord-56488a21aade4e12af1a6cbde7d0bad5
출처 데이터셋
uspto-grants-2014_01
특허 번호
US08637536B2

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