Sodium Hydroxide → (S,E)-6-(1-(tert-butoxy)-2-ethoxy-2-oxoethyl)-5-methyl-7-(4-methylpent-1-en-1-yl)pyrazolo[1,5-a]pyrimidine-2-carboxylic acid

HRID 1630325ノート

反応式

HRID 1630325 の反応式
[C:1]([O:5][C@@H:6]([C:12]1[C:13]([CH3:32])=[N:14][C:15]2[N:16]([N:24]=[C:25]([C:27]([O:29]CC)=[O:28])[CH:26]=2)[C:17]=1/[CH:18]=[CH:19]/[CH2:20][CH:21]([CH3:23])[CH3:22])[C:7]([O:9][CH2:10][CH3:11])=[O:8])([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+]>CCO>[C:1]([O:5][C@@H:6]([C:12]1[C:13]([CH3:32])=[N:14][C:15]2[N:16]([N:24]=[C:25]([C:27]([OH:29])=[O:28])[CH:26]=2)[C:17]=1/[CH:18]=[CH:19]/[CH2:20][CH:21]([CH3:22])[CH3:23])[C:7]([O:9][CH2:10][CH3:11])=[O:8])([CH3:3])([CH3:4])[CH3:2]

参加物

4

反応物 2

HCID 14798Sodium HydroxideHCID 71267861(S,E)-Ethyl 6-(1-(tert-butoxy)-2-ethoxy-2-oxoethyl)-5-methyl-7-(4-methylpent-1-en-1-yl)pyrazolo[1,5-a]pyrimidine-2-carboxylate

生成物 1

HCID 71259118(S,E)-6-(1-(tert-butoxy)-2-ethoxy-2-oxoethyl)-5-methyl-7-(4-methylpent-1-en-1-yl)pyrazolo[1,5-a]pyrimidine-2-carboxylic acid収率 81.5%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

To a solution of (S,E)-ethyl 6-(1-(tert-butoxy)-2-ethoxy-2-oxoethyl)-5-methyl-7-(4-methylpent-1-en-1-yl)pyrazolo[1,5-a]pyrimidine-2-carboxylate (190 mg, 0.426 mmol) in EtOH (4 mL) was added 1N NaOH (0.426 mL, 0.426 mmol) and the resulting mixture was stirred at room temp for 4 h. At this point LCMS indicated completion of reaction. Solvents were then removed under reduced pressure and the mixture was diluted with water (3 mL), acidified with 1N HCl, extracted with ethyl acetate (25 mL), washed with brine (10 mL), dried (Na2SO4), filtered and concentrated to afford (S,E)-6-(1-(tert-butoxy)-2-ethoxy-2-oxoethyl)-5-methyl-7-(4-methylpent-1-en-1-yl)pyrazolo[1,5-a]pyrimidine-2-carboxylic acid (145 mg, 0.347 mmol, 81% yield) as light yellow solid. 1H NMR (500 MHz, CDCl3) δ 7.20 (s, 1H), 7.01 (d, J=16.1 Hz, 1H), 6.90 (br. s., 1H), 5.57 (s, 1H), 4.48 (d, J=7.3 Hz, 1H), 4.30-4.22 (m, 2H), 2.72 (br. s., 3H), 2.00-1.85 (m, 1H), 1.32-1.25 (m, 3H), 1.18 (s, 9H), 1.10-0.97 (m, 6H). LCMS (M+H)=418.4.

後処理

  1. customcompletion of reaction
  2. customSolvents were then removed under reduced pressure
  3. additionthe mixture was diluted with water (3 mL)
  4. extractionextracted with ethyl acetate (25 mL)
  5. washwashed with brine (10 mL)
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated

出典と根拠

ORDレコード
ord-0aa86a9068d3420d8af72f3ab17b6278
出典データセット
uspto-grants-2014_07
特許番号
US08791108B2

反応ノート

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