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

HRID 705975노트

반응식

HRID 705975 반응식
[H-].[Na+].CO[C:5](=[O:15])[CH2:6][CH2:7][C:8]1[CH:9]=[N:10][C:11]([CH3:14])=[N:12][CH:13]=1.[CH:16](OC)=O.[NH2:20][C:21]([NH2:23])=[S:22]>COCCOC.C(OCC)C>[CH3:14][C:11]1[N:12]=[CH:13][C:8]([CH2:7][C:6]2[C:5](=[O:15])[NH:20][C:21](=[S:22])[NH:23][CH:16]=2)=[CH:9][N:10]=1

참가 물질

7

반응물 4

HCID 7865Methyl formateHCID 24758Sodium hydrideHCID 2723790ThioureaHCID 677746633-(2-Methyl-pyrimidin-5-yl)-propionic acid methyl ester

생성물 1

HCID 205833715-(2-Methyl-pyrimidin-5-ylmethyl)-2-thioxo-2,3-dihydro-1H-pyrimidin-4-one수율 35.9%

시약·촉매·용매 2

HCID 3283Diethyl Ether용매HCID 80711,2-Dimethoxyethane용매2회

실험 절차

To the suspension of NaH, 60% (1.3 eq, 130 mg) in 600 μl of dry 1,2-dimethoxyethane, under argon atmosphere was carefully added, via syringe, a solution of 3-(2-Methyl-pyrimidin-5-yl)-propionic acid methyl ester (450 mg, 2.5 mmol, 1 eq) and methyl formate (4 eq, 616 μl) in 3 ml of dry 1,2-dimethoxyethane. The resulting suspension was stirred overnight (16 hours) at room temperature. In the reaction mixture was then added 3 ml of dry diethyl ether. The resulting precipitate was collected; it was washed with 3 ml of diethyl ether and dried. It was dissolved in 4 ml of absolute ethanol, thiourea (1.5 eq, 285 mg) was added and the reaction mixture was stirred at reflux under argon atmosphere for 8 hours. Solvent was then evaporated, the rest was dissolved in 3 ml of water and pH value of the solution was adjusted to 4.5-5 using 3N HCl water solution. The resulting precipitate was collected, it was washed with water and dried to afford 5-(2-Methyl-pyrimidin-5-ylmethyl)-2-thioxo-2,3-dihydro-1H-pyrimidin-4-one (210 mg, yield=35.9%, purity=95%) in form of white powder. MS: [M+H]+=235.17 1H NMR (300 MHz; DMSO-d6) δ/ppm 2.54 (s, 3H), 3.50 (s, 2H), 7.48 (s, 1H), 8.55 (s, 2H), 12.38 (br.s., 2H)

후처리

  1. additionunder argon atmosphere was carefully added, via syringe
  2. customThe resulting precipitate was collected
  3. washit was washed with 3 ml of diethyl ether
  4. customdried
  5. dissolutionIt was dissolved in 4 ml of absolute ethanol
  6. stirringthe reaction mixture was stirred
  7. temperatureat reflux under argon atmosphere for 8 hours
  8. customSolvent was then evaporated
  9. dissolutionthe rest was dissolved in 3 ml of water
  10. customThe resulting precipitate was collected
  11. washit was washed with water
  12. customdried

출처 및 근거

ORD 기록
ord-d1035fcb9a264c61b58074de64b068d8
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09174968B2

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