Methyl iodide → (2-Cyclopropyl-4-methyl-7-oxo-4,7-dihydro-pyrazolo[1,5-a]pyrimidin-6-yl)-acetic acid ethyl ester

HRID 57794노트

반응식

HRID 57794 반응식
[CH2:1]([O:3][C:4](=[O:19])[CH2:5][C:6]1[C:11](=[O:12])[N:10]2[N:13]=[C:14]([CH:16]3[CH2:18][CH2:17]3)[CH:15]=[C:9]2[NH:8][CH:7]=1)[CH3:2].[H-].[Na+].[CH3:22]I>O1CCCC1.C(OCC)(=O)C.O>[CH2:1]([O:3][C:4](=[O:19])[CH2:5][C:6]1[C:11](=[O:12])[N:10]2[N:13]=[C:14]([CH:16]3[CH2:17][CH2:18]3)[CH:15]=[C:9]2[N:8]([CH3:22])[CH:7]=1)[CH3:2]

참가 물질

7

반응물 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 178470741HCID 178470741, 화합물

생성물 1

HCID 86702935(2-Cyclopropyl-4-methyl-7-oxo-4,7-dihydro-pyrazolo[1,5-a]pyrimidin-6-yl)-acetic acid ethyl ester수율 59%

시약·촉매·용매 3

HCID 962Water용매HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

실험 절차

To a suspension of (2-cyclopropyl-7-oxo-4,7-dihydro-pyrazolo[1,5-a]pyrimidin-6-yl)-acetic acid ethyl ester (80 mg, 0.3 mmol, 1 eq) described in example 90 in tetrahydrofuran (2 mL) was added sodium hydride (16 mg, 3.9 mmol, 1.3 eq). The mixture was stirred during 30 min at room temperature and methyl iodide (30 μL, 0.5 mmol, 1.5 eq) was added. The mixture was stirred at room temperature for 5 h. The mixture was then diluted with ethyl acetate (5 mL) and water (5 mL) was added. The aqueous layer was extracted with ethyl acetate (2×10 mL) and the aqueous phases were dried over magnesium sulfate, filtered and evaporated in vacuo. The crude residue was purified by flash chromatography using cyclohexane and ethyl acetate (100/0 to 0/100) to afford the expected compound as white powder (16 mg, 59% yield).

후처리

  1. stirringThe mixture was stirred at room temperature for 5 h
  2. additionwas added
  3. extractionThe aqueous layer was extracted with ethyl acetate (2×10 mL)
  4. dry with materialthe aqueous phases were dried over magnesium sulfate
  5. filtrationfiltered
  6. customevaporated in vacuo
  7. customThe crude residue was purified by flash chromatography

출처 및 근거

ORD 기록
ord-30351e5ad1044d5ab24c54b5b25da183
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09434745B2

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