Hydrochloric Acid → Ethyl 3-methyl-2,4-dioxo-1-propyl-1,2,3,4-tetrahydrothieno[2,3-d]pyrimidine-5-carboxylate

HRID 131572노트

반응식

HRID 131572 반응식
[CH3:1][N:2]1[C:7](=[O:8])[CH:6]=[C:5]([SH:9])[N:4]([CH2:10][CH2:11][CH3:12])[C:3]1=[O:13].C(=O)([O-])[O-].[K+].[K+].Br[CH2:21][C:22](=O)[C:23]([O:25][CH2:26][CH3:27])=[O:24].Cl>CN(C)C=O.ClCCl.[Ti](Cl)(Cl)(Cl)Cl.O>[CH3:1][N:2]1[C:7](=[O:8])[C:6]2[C:22]([C:23]([O:25][CH2:26][CH3:27])=[O:24])=[CH:21][S:9][C:5]=2[N:4]([CH2:10][CH2:11][CH3:12])[C:3]1=[O:13]

참가 물질

9

반응물 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 66144Ethyl bromopyruvateHCID 866227106-Mercapto-3-methyl-1-propyl-pyrimidine-2,4(1H,3H)-dione

생성물 1

HCID 17974732Ethyl 3-methyl-2,4-dioxo-1-propyl-1,2,3,4-tetrahydrothieno[2,3-d]pyrimidine-5-carboxylate

시약·촉매·용매 4

HCID 24193Titanium Tetrachloride촉매HCID 962Water용매2회HCID 6228Dimethylformamide용매HCID 6344Dichloromethane용매

실험 절차

The product of step b) (6.95 g) in dry dimethylformamide (100 ml) was added potassium carbonate (2.4 g) and stirred for 10 min. Ethyl bromopyruvate (5 ml) was added and was stirred under nitrogen at room temperature for 2 h. The reaction was poured into water (1 L), acidified (2M HCl) and extracted with ethyl acetate. The organic extracts were washed with brine (100 ml). Drying and evaporation afforded an oil. The oil was dissolved in dichloromethane (100 ml) and cooled in ice whilst stirring. Titanium tetrachloride (7.58 ml) was added and stirring continued under nitrogen for 2 h. The reaction was poured into water (1 L) and extracted with dichloromethane. The organics were dried and evaporated in vacuo. The residue was purified by chromatography (SiO2/ethyl acetate-dichloromethane 0-8%) to afford the subtitle compound as an orange oil, 4.64 g. δ 1HCDCl3 1.02 (3H, t), 1.83 (2H, sextet), 3.42 (3H, s), 3.95 (2H, t), 4.41 (2H, q), 7.30 (1H, s). MS (APCI) 297.1 (M++H)

후처리

  1. stirringwas stirred under nitrogen at room temperature for 2 h
  2. extractionextracted with ethyl acetate
  3. washThe organic extracts were washed with brine (100 ml)
  4. customDrying
  5. customevaporation
  6. customafforded an oil
  7. temperaturecooled in ice
  8. stirringwhilst stirring
  9. stirringstirring
  10. waitcontinued under nitrogen for 2 h
  11. extractionextracted with dichloromethane
  12. customThe organics were dried
  13. customevaporated in vacuo
  14. customThe residue was purified by chromatography (SiO2/ethyl acetate-dichloromethane 0-8%)

출처 및 근거

ORD 기록
ord-ee08f61483ce4b388c418c3d2681ec37
출처 데이터셋
uspto-grants-2008_06
특허 번호
US07384950B2

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