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Ethyl Acetate → 7-(1-aminoethyl)-3-methyl-6-(1,3-thiazol-4-yl)-5H-[1,3]thiazolo[3,2-a]pyrimidin-5-one

HRID 58260
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HRID 58260 반응식
[N:1]([CH:4]([C:6]1[N:7]=[C:8]2[S:20][CH:19]=[C:18]([CH3:21])[N:9]2[C:10](=[O:17])[C:11]=1[C:12]1[N:13]=[CH:14][S:15][CH:16]=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:20][CH:19]=[C:18]([CH3:21])[N:9]2[C:10](=[O:17])[C:11]=1[C:12]1[N:13]=[CH:14][S:15][CH:16]=1)[CH3:5]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 3

HCID 8857Ethyl AcetateHCID 68983TrimethylphosphineHCID 866500697-(1-azidoethyl)-3-methyl-6-(1,3-thiazol-4-yl)-5H-[1,3]thiazolo[3,2-a]pyrimidin-5-one

생성물 1

HCID 581114467-(1-aminoethyl)-3-methyl-6-(1,3-thiazol-4-yl)-5H-[1,3]thiazolo[3,2-a]pyrimidin-5-one

시약·촉매·용매 2

HCID 962Water용매
HCID 8028
Tetrahydrofuran
용매
2회

실험 절차

To a stirred solution of 7-(1-azidoethyl)-3-methyl-6-(1,3-thiazol-4-yl)-5H-[1,3]thiazolo[3,2-a]pyrimidin-5-one (0.030 g, 0.094 mmol) in tetrahydrofuran (0.3 mL) and water (0.068 mL) was added 1.00 M of trimethylphosphine in tetrahydrofuran (0.113 mL, 0.113 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 1 N HCl two times. The combined extracts were neutralized with solid sodium bicarbonate, and extracted with dichloromethane. The combined organic layers were washed with brine, dried over magnesium sulfate, and concentrated under reduced pressure. The residue was used directly in next step. LCMS calculated for C12H13N4OS2(M+H)+: m/z=293.1. Found: 293.0.

후처리

  1. extractionthe mixture was extracted with 1 N HCl two times
  2. extractionextracted with dichloromethane
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-32cbe07549ee4e9eae65573e2a465441
출처 데이터셋
uspto-grants-2016_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09434746B2

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