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

HRID 57794ノート

反応式

HRID 57794 の反応式
[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]

参加物

7

反応物 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 178470741HCID 178470741、化合物

生成物 1

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

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-30351e5ad1044d5ab24c54b5b25da183
出典データセット
uspto-grants-2016_09
特許番号
US09434745B2

反応ノート

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