Triethylamine → n-Hydroxypyrimidine-5-carboximidamide

HRID 2415757노트

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HRID 2415757 반응식
[C:1]([C:3]1[CH:4]=[N:5][CH:6]=[N:7][CH:8]=1)#[N:2].Cl.[NH2:10][OH:11].C(N(CC)CC)C.Cl.C(N(CC)CC)C>CO>[OH:11][N:10]=[C:1]([C:3]1[CH:4]=[N:5][CH:6]=[N:7][CH:8]=1)[NH2:2]

참가 물질

6

반응물 4

HCID 8471TriethylamineHCID 11130Triethylamine hydrochlorideHCID 443297Hydroxyamine hydrochlorideHCID 10197646Pyrimidine-5-carbonitrile

생성물 1

HCID 34181140n-Hydroxypyrimidine-5-carboximidamide수율 52.2%

시약·촉매·용매 1

HCID 887Methanol용매

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온도
0 °C

실험 절차

5-Cyanopyrimidine (J. Org. Chem. 1962, 27, 2264) (0.64 g, 6.1 mmol) was dissolved in methanol (20 mL), the solution was cooled to 0° C. then hydroxylamine hydrochloride (0.42 g, 6.1 mmol) and triethylamine (0.84 mL, 6.1 mmol) were added and the mixture was heated to reflux overnight. The mixture was cooled to room temperature, and the solvent was removed in vacuo. The residue was pre-absorbed onto silica gel, and purified by flash chromatography on silica gel (dichloromethane/methanol/aqueous ammonia—95:5:0.5 as eluant) to give a yellow solid which was contaminated with triethylamine hydrochloride. Recrystallisation from ethanol gave the title compound as a white solid (0.44 g).

후처리

  1. temperaturethe mixture was heated
  2. temperatureto reflux overnight
  3. temperatureThe mixture was cooled to room temperature
  4. customthe solvent was removed in vacuo
  5. customThe residue was pre-absorbed onto silica gel
  6. custompurified by flash chromatography on silica gel (dichloromethane/methanol/aqueous ammonia—95:5:0.5 as eluant)
  7. customto give a yellow solid which
  8. customRecrystallisation from ethanol

출처 및 근거

ORD 기록
ord-a93ff3a5d7bf4bb0a869ab4bbd72fe5b
출처 데이터셋
uspto-grants-2004_11
특허 번호
US06821972B2

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