Water → Methyl [4-methyl-2-(4-nitrobenzyl)-6-pyrrolidin-1-ylpyrimidin-5-yl]acetate

HRID 1159675

반응식

HRID 1159675 반응식
Cl[C:2]1[C:7]([CH2:8][C:9]([O:11][CH3:12])=[O:10])=[C:6]([CH3:13])[N:5]=[C:4]([CH2:14][C:15]2[CH:20]=[CH:19][C:18]([N+:21]([O-:23])=[O:22])=[CH:17][CH:16]=2)[N:3]=1.[NH:24]1[CH2:28][CH2:27][CH2:26][CH2:25]1.C(N(CC)CC)C.O>CN(C=O)C>[CH3:13][C:6]1[C:7]([CH2:8][C:9]([O:11][CH3:12])=[O:10])=[C:2]([N:24]2[CH2:28][CH2:27][CH2:26][CH2:25]2)[N:3]=[C:4]([CH2:14][C:15]2[CH:20]=[CH:19][C:18]([N+:21]([O-:23])=[O:22])=[CH:17][CH:16]=2)[N:5]=1

참가 물질

6

반응물 4

HCID 962WaterHCID 8471TriethylamineHCID 31268PyrrolidineHCID 59514487Methyl [4-chloro-6-methyl-2-(4-nitrobenzyl)pyrimidin-5-yl]acetate

생성물 1

HCID 59514538Methyl [4-methyl-2-(4-nitrobenzyl)-6-pyrrolidin-1-ylpyrimidin-5-yl]acetate수율 83.1%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
85 °C

실험 절차

A solution of methyl [4-chloro-6-methyl-2-(4-nitrobenzyl)pyrimidin-5-yl]acetate (0.45 g, 1.3 mmol) and pyrrolidine (0.13 mL, 1.6 mmol) in DMF (10 mL) at room temperature was treated with triethylamine (0.22 mL, 1.6 mmol) and the resulting mixture was stirred at 85° C. for 13 hours. After cooling to room temperature, the reaction mixture was poured into water and extracted with EtOAc. The combined organic extracts was washed with saturated NaHCO3 and brine, dried over anhydrous MgSO4, filtered, and concentrated in vacuo. The crude product thus obtained was chromatographed over silica gel eluting with 50% EtOAc in CH2Cl2 to give methyl [4-methyl-2-(4-nitrobenzyl)-6-pyrrolidin-1-ylpyrimidin-5-yl]acetate (0.40 g, 80% yield) as a white powder.

후처리

  1. temperatureAfter cooling to room temperature
  2. extractionextracted with EtOAc
  3. washThe combined organic extracts was washed with saturated NaHCO3 and brine
  4. dry with materialdried over anhydrous MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe crude product thus obtained
  8. customwas chromatographed over silica gel eluting with 50% EtOAc in CH2Cl2

출처 및 근거

ORD 기록
ord-36a89892833b45c093966ecee4475613
출처 데이터셋
uspto-grants-2010_10
특허 번호
US07812160B2

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