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Methyl formate → 5-(6-methoxy-pyridin-3-ylmethyl)-2-thioxo-2,3-dihydro-1H-pyrimidin-4-one

HRID 474756
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HRID 474756 반응식
[H-].[Na+].CO[C:5](=[O:16])[CH2:6][CH2:7][C:8]1[CH:9]=[N:10][C:11]([O:14][CH3:15])=[CH:12][CH:13]=1.[CH:17](OC)=O.[NH2:21][C:22]([NH2:24])=[S:23]>COCCOC>[CH3:15][O:14][C:11]1[N:10]=[CH:9][C:8]([CH2:7][C:6]2[C:5](=[O:16])[NH:21][C:22](=[S:23])[NH:24][CH:17]=2)=[CH:13][CH:12]=1
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참가 물질

6

반응물 4

HCID 7865Methyl formateHCID 24758Sodium hydrideHCID 2723790ThioureaHCID 22009636Methyl 3-(2-methoxy-5-pyridyl)propionate

생성물 1

HCID 866662255-(6-methoxy-pyridin-3-ylmethyl)-2-thioxo-2,3-dihydro-1H-pyrimidin-4-one수율 49.8%

시약·촉매·용매 1

HCID 8071
1,2-Dimethoxyethane
용매
2회

실험 절차

To a suspension of NaH, 60% dispersion on mineral oil (1.3 eq, 110 mg, 60%) in 700 μl of dry 1,2-dimethoxyethane under argon atmosphere was added a solution of 3-(6-Methoxy-pyridin-3-yl)-propionic acid methyl ester (590 mg, 3.02 mmol, 1 eq) and methyl formate (2 eq, 380 μl) in 4 ml of dry 1,2-dimethoxyethane. The sealed mixture was stirred at room temperature for 16 hours (overnight). Solvent from the mixture was then evaporated. In the rest was added 15 ml of diethyl ether and using ultrasound bath the precipitate was formed. The liquor was removed and in the rest was triturated once more with diethyl ether. The precipitate was dried and was dissolved in 5 ml of absolute ethanol, thiourea (1.5 eq, 345 mg) was added and the resulting mixture was heated at 90° C. (temperature on display of heating device) for 2 hours. The solvent was evaporated and the rest was dissolved in 5 ml of water. pH of the solution was adjusted to 6-7 and the formed precipitate was collected by filtration and was dried to afford 5-(6-methoxy-pyridin-3-ylmethyl)-2-thioxo-2,3-dihydro-1H-pyrimidin-4-one (395 mg, yield=49.8%, purity=95%). MS: [M+H]+=250.18 1H NMR (300 MHz; DMSO-d6) δ/ppm 3.45 (s, 2H), 3.80 (s, 3H), 6.70 (d, J=8.36 Hz, 1H), 7.42 (s, 1H), 7.55 (dd, J=8.36 Hz, J=2.40 Hz, 1H), 8.05 (d, J=2.40 Hz, 1H), 12.10-12.60 (m, 2H)

후처리

  1. customSolvent from the mixture was then evaporated
  2. additionIn the rest was added 15 ml of diethyl ether
  3. customwas formed
  4. customThe liquor was removed and in the rest
  5. customwas triturated once more with diethyl ether
  6. customThe precipitate was dried
  7. dissolutionwas dissolved in 5 ml of absolute ethanol
  8. temperaturethe resulting mixture was heated at 90° C.
  9. temperature(temperature on display of heating device) for 2 hours
  10. customThe solvent was evaporated
  11. dissolutionthe rest was dissolved in 5 ml of water
  12. filtrationthe formed precipitate was collected by filtration
  13. customwas dried

출처 및 근거

ORD 기록
ord-b663f134df2f45a8843bc90b4ee7c1f6
출처 데이터셋
uspto-grants-2014_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08637536B2

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