Triethylamine → 2-Cyclopropylpyrimidine-4-carbonitrile

HRID 931260노트

반응식

HRID 931260 반응식
[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

참가 물질

7

반응물 4

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

생성물 1

HCID 898530762-Cyclopropylpyrimidine-4-carbonitrile수율 62%

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

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온도
50 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-c17d46817fa241b5a9946d14838037ad
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09296745B2

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