Triethylamine → 2-Cyclopropylpyrimidine-4-carbonitrile

HRID 931260ノート

反応式

HRID 931260 の反応式
[CH:1]1([C:4]2[N:9]=[C:8]([CH:10]=O)[CH:7]=[CH:6][N:5]=2)[CH2:3][CH2:2]1.Cl.NO.C([N:17](CC)CC)C.CCCP(=O)=O>CN(C)C=O.O>[CH:1]1([C:4]2[N:9]=[C:8]([C:10]#[N:17])[CH:7]=[CH:6][N:5]=2)[CH2:3][CH2:2]1

参加物

7

反応物 4

HCID 8471TriethylamineHCID 443297Hydroxyamine hydrochlorideHCID 16167369Propylphosphoric anhydrideHCID 299398122-Cyclopropylpyrimidine-4-carbaldehyde

生成物 1

HCID 898530762-Cyclopropylpyrimidine-4-carbonitrile収率 62%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

反応条件

温度
50 °C

実験手順

To a solution of 2-cyclopropylpyrimidine-4-carbaldehyde (1.0 g, 6.68 mmol) in N,N-dimethylformamide (10 mL) were added hydroxylamine hydrochloride (500 mg, 7.02 mmol) and triethylamine (1.2 mL). The reaction mixture was heated to 50° C. and propylphosphonic anhydride (T3P) was added dropwise. After 16 h at 110° C., the mixture was cooled to room temperature, diluted with water and quenched with solid sodium bicarbonate. The mixture was extracted with ethyl acetate, then the organic layer was dried over sodium sulfate, filtered, concentrated under reduced pressure. The residue was purified via silica gel chromatography to afford 2-cyclopropylpyrimidine-4-carbonitrile (600 mg, 62%) as a pale yellow liquid. MS (ES+APCI) (M+H) 145.9; LMCS retention time 2.224 min (Method G).

後処理

  1. temperaturethe mixture was cooled to room temperature
  2. customquenched with solid sodium bicarbonate
  3. extractionThe mixture was extracted with ethyl acetate
  4. dry with materialthe organic layer was dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified via silica gel chromatography

出典と根拠

ORDレコード
ord-c17d46817fa241b5a9946d14838037ad
出典データセット
uspto-grants-2016_03
特許番号
US09296745B2

反応ノート

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