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

HRID 411286ノート

反応式

HRID 411286 の反応式
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

参加物

8

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 3283Diethyl Ether溶媒HCID 3776Isopropanol溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-24fb2ec41368418e88d78042f0d9af3d
出典データセット
uspto-grants-2003_05
特許番号
US06559155B1

反応ノート

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