Methyl formate → 5-(2-Methoxypyrimidin-5-ylmethyl)-2-thiouracil

HRID 411286노트

반응식

HRID 411286 반응식
CC(C)([O-])C.[K+].[CH3:7][O:8][C:9]1[N:14]=[CH:13][C:12]([CH2:15][CH2:16][C:17]([O:19]CC)=O)=[CH:11][N:10]=1.[CH:22](OC)=O.[NH2:26][C:27]([NH2:29])=[S:28]>C1COCC1.CCOCC.CC(O)C>[CH3:7][O:8][C:9]1[N:10]=[CH:11][C:12]([CH2:15][C:16]2[C:17](=[O:19])[NH:26][C:27](=[S:28])[NH:29][CH:22]=2)=[CH:13][N:14]=1

참가 물질

8

반응물 4

HCID 7865Methyl formateHCID 2723790ThioureaHCID 21936233Ethyl 3-(2-methoxypyrimidin-5-yl)propionateHCID 23665647Potassium tert-butoxide

생성물 1

HCID 219362445-(2-Methoxypyrimidin-5-ylmethyl)-2-thiouracil

시약·촉매·용매 3

HCID 3283Diethyl Ether용매HCID 3776Isopropanol용매HCID 8028Tetrahydrofuran용매

실험 절차

To an ice cooled solution of potassium t-butoxide (7.83 g, 0.07 mol) in anhydrous THF (60 ml) was added dropwise with stirring under argon over 1 hour to a solution of ethyl 3-(2-methoxypyrimidin-5-yl)propionate (5.87 g, 0.028 mol) and methyl formate (3.6 ml, 0.059 mol) in anhydrous ether (70 ml). After stirring for 16 h, the solvents were evaporated, thiourea (4.25 g, 0.056 mol) and propan-2-ol (80 ml) added and the mixture refluxed for 5 h. The solvent was evaporated and the residue dissolved in water, extracted twice with ether and acidified to pH 4.5 with acetic acid. The solid which precipitated was filtered, washed well with water and dried, yield 5.57 g (80%). 1H-NMR (d6-DMSO) δ3.47 (2H, s), 3.85 (3H, s), 7.43 (1H, s), 8.48 (2H, s), 12.25 (1H, br s), 12.46 (1H, br s); MS (APCI+) found (M+H)=251; C10H10N4O2S requires 250.

후처리

  1. customthe solvents were evaporated
  2. temperaturethe mixture refluxed for 5 h
  3. customThe solvent was evaporated
  4. dissolutionthe residue dissolved in water
  5. extractionextracted twice with ether
  6. customThe solid which precipitated
  7. filtrationwas filtered
  8. washwashed well with water
  9. customdried

출처 및 근거

ORD 기록
ord-24fb2ec41368418e88d78042f0d9af3d
출처 데이터셋
uspto-grants-2003_05
특허 번호
US06559155B1

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