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

HRID 1685192ノート

反応式

HRID 1685192 の反応式
[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

参加物

4

反応物 3

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

生成物 1

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

反応条件

温度
100 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-6715b2f750b8489ca30caccf4e1c4ad4
出典データセット
uspto-grants-2012_04
特許番号
US08148387B2

反応ノート

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