Water → Ethyl 4-((1-(tert-butoxycarbonyl)pyrrolidin-3-yl)methylamino)-2-chloropyrimidine-5-carboxylate

HRID 384264

반응식

HRID 384264 반응식
[Cl:1][C:2]1[N:7]=[C:6](Cl)[C:5]([C:9]([O:11][CH2:12][CH3:13])=[O:10])=[CH:4][N:3]=1.[C:14]([N:21]1[CH2:25][CH2:24][CH:23]([CH2:26][NH2:27])[CH2:22]1)([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15].CCN(C(C)C)C(C)C.O>CC#N.CCOC(C)=O>[C:17]([O:16][C:14]([N:21]1[CH2:25][CH2:24][CH:23]([CH2:26][NH:27][C:6]2[C:5]([C:9]([O:11][CH2:12][CH3:13])=[O:10])=[CH:4][N:3]=[C:2]([Cl:1])[N:7]=2)[CH2:22]1)=[O:15])([CH3:20])([CH3:19])[CH3:18]

참가 물질

7

반응물 4

HCID 962WaterHCID 81531DiisopropylethylamineHCID 104020Ethyl 2,4-dichloropyrimidine-5-carboxylateHCID 2756485tert-Butyl 3-(aminomethyl)pyrrolidine-1-carboxylate

생성물 1

HCID 58098693Ethyl 4-((1-(tert-butoxycarbonyl)pyrrolidin-3-yl)methylamino)-2-chloropyrimidine-5-carboxylate수율 94.2%

시약·촉매·용매 2

HCID 6342Acetonitrile용매HCID 8857Ethyl Acetate용매

실험 절차

The mixture of ethyl 2,4-dichloropyrimidine-5-carboxylate (332 mg, 1.50 mmol), 1-Boc-3-aminomethylpyrrolidine (300 mg, 1.50 mmol) and DIEA (0.650 mL, 3.73 mmol) in CH3CN (6 mL) was stirred at room temperature for 18 h. Water and EtOAc were added. The organic phase was separated, washed with 1N HCl, then with 5% NaHCO3, dried over Na2SO4, concentrated in vacuo to give ethyl 4-((1-(tert-butoxycarbonyl)pyrrolidin-3-yl)methylamino)-2-chloropyrimidine-5-carboxylate (544 mg).

후처리

  1. customThe organic phase was separated
  2. washwashed with 1N HCl
  3. dry with materialwith 5% NaHCO3, dried over Na2SO4
  4. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-000f5f35b8dc4f65bb68b9eb6ccd87bd
출처 데이터셋
uspto-grants-2013_02
특허 번호
US08367689B2

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