Ethyl Acetate → 7-(1-aminoethyl)-6-phenyl-5H-[1,3]thiazolo[3,2-a]pyrimidin-5-one

HRID 1429824ノート

反応式

HRID 1429824 の反応式
[N:1]([CH:4]([C:6]1[N:7]=[C:8]2[S:21][CH:20]=[CH:19][N:9]2[C:10](=[O:18])[C:11]=1[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[CH3:5])=[N+]=[N-].CP(C)C.C(OCC)(=O)C>O1CCCC1.O>[NH2:1][CH:4]([C:6]1[N:7]=[C:8]2[S:21][CH:20]=[CH:19][N:9]2[C:10](=[O:18])[C:11]=1[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[CH3:5]

参加物

6

反応物 3

HCID 8857Ethyl AcetateHCID 68983TrimethylphosphineHCID 866500747-(1-azidoethyl)-6-phenyl-5H-[1,3]thiazolo[3,2-a]pyrimidin-5-one

生成物 1

HCID 581114357-(1-aminoethyl)-6-phenyl-5H-[1,3]thiazolo[3,2-a]pyrimidin-5-one収率 62.2%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒2 回

実験手順

To a stirred solution of 7-(1-azidoethyl)-6-phenyl-5H-[1,3]thiazolo[3,2-a]pyrimidin-5-one (0.23 g, 0.77 mmol) in tetrahydrofuran (5 mL) and water (1 mL) was added 1.00 M of trimethylphosphine in tetrahydrofuran (0.93 mL, 0.93 mmol) at room temperature, and the mixture was stirred at room temperature for 1 hour. To the mixture was added ethyl acetate, and the mixture was extracted with aqueous 1N HCl solution (three times). The combined extract was neutralized with solid NaHCO3 and extracted with dichloromethane (two times). The combined organic layer was washed with brine, dried over Na2SO4, and concentrated to give the desired compound (0.13 g, 62%). LCMS calculated for C14H14N3OS (M+H)+: m/z=272.1. Found: 272.0.

後処理

  1. extractionthe mixture was extracted with aqueous 1N HCl solution (three times)
  2. extractionThe combined extract
  3. extractionextracted with dichloromethane (two times)
  4. washThe combined organic layer was washed with brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated

出典と根拠

ORDレコード
ord-5db1ab83479b42409dec87e11b85f512
出典データセット
uspto-grants-2015_01
特許番号
US08940752B2

反応ノート

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