Azetidine → 4-(Azetidin-1-yl)-6-chloropyrimidine-5-carbaldehyde

HRID 72708

반응식

HRID 72708 반응식
Cl[C:2]1[C:7]([CH:8]=[O:9])=[C:6]([Cl:10])[N:5]=[CH:4][N:3]=1.[NH:11]1[CH2:14][CH2:13][CH2:12]1>C(Cl)(Cl)Cl.C(N(CC)CC)C>[N:11]1([C:2]2[C:7]([CH:8]=[O:9])=[C:6]([Cl:10])[N:5]=[CH:4][N:3]=2)[CH2:14][CH2:13][CH2:12]1

참가 물질

5

반응물 2

HCID 10422AzetidineHCID 8196914,6-Dichloro-5-pyrimidinecarbaldehyde

생성물 1

HCID 867125624-(Azetidin-1-yl)-6-chloropyrimidine-5-carbaldehyde

시약·촉매·용매 2

HCID 8471Triethylamine촉매HCID 6212Chloroform용매

실험 절차

To a solution of 4,6-dichloropyrimidine-5-carbaldehyde (1.00 g, 5.65 mmol) in chloroform at 0° C. were added azetidine (99%, 0.392 mL, 5.71 mmol) and triethylamine (5 drops). The reaction mixture was allowed to warm to room temperature and then stirred for 18 hours. The reaction mixture was filtered, and the filtrate was purified by silica gel chromatography (Gradient: 0% to 100% ethyl acetate in heptane) to provide the product. Yield: 880 mg, 4.45 mmol, 79%. LCMS m/z 198.1, 200.1 (M+1). 1H NMR (400 MHz, CD3OD) δ 2.34-2.43 (m, 2H), 4.12-4.33 (br m, 4H), 8.30 (s, 1H), 10.28 (s, 1H).

후처리

  1. filtrationThe reaction mixture was filtered
  2. customthe filtrate was purified by silica gel chromatography (Gradient: 0% to 100% ethyl acetate in heptane)
  3. customto provide the product

출처 및 근거

ORD 기록
ord-50b2e28456f84a5494615235ad31a5bc
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08829010B2

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