Hydrochloric Acid → 4-Chloro-7-(4-methoxybenzyl)-5H-pyrrolo[2,3-d]pyrimidin-6(7H)-one

HRID 1685192노트

반응식

HRID 1685192 반응식
[Cl:1][C:2]1[C:7]([CH2:8][C:9](OC)=[O:10])=[C:6]([NH:13][CH2:14][C:15]2[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=2)[N:5]=[CH:4][N:3]=1.Cl.O>>[Cl:1][C:2]1[C:7]2[CH2:8][C:9](=[O:10])[N:13]([CH2:14][C:15]3[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=3)[C:6]=2[N:5]=[CH:4][N:3]=1

참가 물질

4

반응물 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 86641609Methyl 2-(4-chloro-6-(4-methoxybenzylamino)pyrimidin-5-yl)acetate

생성물 1

HCID 866416104-Chloro-7-(4-methoxybenzyl)-5H-pyrrolo[2,3-d]pyrimidin-6(7H)-one수율 76.4%

반응 조건

온도
100 °C

실험 절차

Add a solution of methyl 2-(4-chloro-6-(4-methoxybenzylamino)pyrimidin-5-yl)acetate (16.21 g, 1.00 equiv; 50.38 mmol) to HCl (4M in dioxane) (126 mL; 10 equiv; 503.79 mmol) and water (4.54 mL; 5 equiv; 251.89 mmol) and stir at 100° C. for 2 h. Remove dioxane in vacuo and extract with EA. Wash the organic layer with saturated NaHCO3, water, then brine. Dry over MgSO4, filter and concentrate in vacuo. Purify the residue by ISCO 330 g using EA:hex 20 to 70% as eluent to obtain the title compound (11.15 g; 38.49 mmol; 76.39%) as a yellow solid. 1H NMR (300 MHz, DMSO): 8.65 (s, 1H), 7.29-7.26 (m, 2H), 6.89-6.85 (m, 2H), 4.79 (s, 2H), 3.80 (s, 2H), 3.71 (s, 3H).

후처리

  1. extractionRemove dioxane in vacuo and extract with EA
  2. washWash the organic layer with saturated NaHCO3, water
  3. dry with materialDry over MgSO4
  4. filtrationfilter
  5. concentrationconcentrate in vacuo
  6. customPurify the residue by ISCO 330 g

출처 및 근거

ORD 기록
ord-6715b2f750b8489ca30caccf4e1c4ad4
출처 데이터셋
uspto-grants-2012_04
특허 번호
US08148387B2

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