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

HRID 72708

反応式

HRID 72708 の反応式
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

参加物

5

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 8471Triethylamine触媒HCID 6212Chloroform溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-50b2e28456f84a5494615235ad31a5bc
出典データセット
uspto-grants-2014_09
特許番号
US08829010B2

関連ノート

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