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

HRID 574341노트

반응식

HRID 574341 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 10908tert-Butyl acetate용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-685702c337b24c2faf6126a573f08962
출처 데이터셋
uspto-grants-2015_05
특허 번호
US09034882B2

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