Dichloromethane → Methyl 2-(2-bromo-7-chloro-5-methylpyrazolo[1,5-a]pyrimidin-6-yl)-2-tert-butoxyacetate

HRID 574341ノート

反応式

HRID 574341 の反応式
[Br:1][C:2]1[CH:18]=[C:5]2[N:6]=[C:7]([CH3:17])[C:8]([CH:11]([OH:16])[C:12]([O:14][CH3:15])=[O:13])=[C:9]([Cl:10])[N:4]2[N:3]=1.C(Cl)Cl.Cl(O)(=O)(=O)=O>C(OC(C)(C)C)(=O)C>[Br:1][C:2]1[CH:18]=[C:5]2[N:6]=[C:7]([CH3:17])[C:8]([CH:11]([O:16][C:8]([CH3:11])([CH3:9])[CH3:7])[C:12]([O:14][CH3:15])=[O:13])=[C:9]([Cl:10])[N:4]2[N:3]=1

参加物

5

反応物 3

HCID 6344DichloromethaneHCID 24247Perchloric AcidHCID 86670271Methyl 2-(2-bromo-7-chloro-5-methylpyrazolo[1,5-a]pyrimidin-6-yl)-2-hydroxyacetate

生成物 1

HCID 86670272Methyl 2-(2-bromo-7-chloro-5-methylpyrazolo[1,5-a]pyrimidin-6-yl)-2-tert-butoxyacetate収率 120%

試薬・触媒・溶媒 1

HCID 10908tert-Butyl acetate溶媒

実験手順

To a suspension of methyl 2-(2-bromo-7-chloro-5-methylpyrazolo[1,5-a]pyrimidin-6-yl)-2-hydroxyacetate (80 mg, 0.239 mmol) in tert-butyl acetate (2 mL) at room temperature was added CH2Cl2 (2 mL) followed by perchloric acid (0.022 mL, 0.359 mmol). The reaction mixture was stirred for 4 h at room temperature. The reaction mixture was quenched with water and diluted with ethyl acetate. The organic phase was washed with saturated NaHCO3 and dried over sodium sulfate. The solvent was evaporated. Purification by silica gel chromatography provided the title compound (56 mg, 59.9%). 1H NMR (500 MHz, MeOD) δ 1.27 (9 H, s), 2.62 (3 H, s), 3.74 (3 H, s), 5.75 (1 H, s), 6.75 (1 H, s).

後処理

  1. customThe reaction mixture was quenched with water
  2. additiondiluted with ethyl acetate
  3. washThe organic phase was washed with saturated NaHCO3
  4. dry with materialdried over sodium sulfate
  5. customThe solvent was evaporated
  6. customPurification by silica gel chromatography

出典と根拠

ORDレコード
ord-685702c337b24c2faf6126a573f08962
出典データセット
uspto-grants-2015_05
特許番号
US09034882B2

反応ノート

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