ホームMCPワークベンチSkills
ホームワークベンチ通知マイページ
llms.txt · MCPガイドプライバシーポリシー · 利用規約 · サポートv1.8.0
  1. ホーム
  2. /反応

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

HRID 705992
ノート
印刷プレビュー

反応式

HRID 705992 の反応式
[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
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8071
1,2-Dimethoxyethane
溶媒
2 回

実験手順

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)

後処理

  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

出典と根拠

ORDレコード
ord-160048f815994fd8bd1b3471776f0650
出典データセット
uspto-grants-2015_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09174968B2

反応ノート

読み込み中…

このページの内容参加物実験手順後処理出典と根拠反応ノート