Toluene → 2-Chloro-5-(1H-tetrazol-5-yl)pyrimidin-4-amine

HRID 555920

반응식

HRID 555920 반응식
[NH2:1][C:2]1[C:7]([C:8]#[N:9])=[CH:6][N:5]=[C:4]([Cl:10])[N:3]=1.[N-:11]=[N+:12]=[N-:13].[Na+].Cl.C(N(CC)CC)C.C1(C)C=CC=CC=1>C(OCC)(=O)C>[Cl:10][C:4]1[N:3]=[C:2]([NH2:1])[C:7]([C:8]2[NH:13][N:12]=[N:11][N:9]=2)=[CH:6][N:5]=1

참가 물질

6

반응물 4

HCID 1140TolueneHCID 11130Triethylamine hydrochlorideHCID 33557Sodium AzideHCID 28011664-Amino-2-chloropyrimidine-5-carbonitrile

생성물 1

HCID 1785084532-Chloro-5-(1H-tetrazol-5-yl)pyrimidin-4-amine수율 43.1%

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

반응 조건

온도
100 °C

실험 절차

Into a sealed tube were added 4-amino-2-chloro-pyrimidine-5-carbonitrile (837 mg, 5.4 mmol), sodium azide (7.1 mmol, 1.3 eq.), triethylamine hydrochloride (7.1 mmol, 1.3 eq.) and 14 mL of toluene. The tube was tightly capped and the reaction was stirred and heated to 100° C. overnight. The mixture was cooled to room temperature, diluted with ethyl acetate, transferred to a separatory funnel and extracted three times with water. The aqueous extractions were combined and acidified to a pH of 4 with concentrated HCl. The precipitate was collected by filtration, washed with acetonitrile, and dried under vacuum to afford 460 mg of the product, which was used without further purification. MS (EI) for C5HClN7: 198 (M+H).

후처리

  1. customThe tube was tightly capped
  2. temperatureThe mixture was cooled to room temperature
  3. customtransferred to a separatory funnel
  4. extractionextracted three times with water
  5. extractionThe aqueous extractions
  6. filtrationThe precipitate was collected by filtration
  7. washwashed with acetonitrile
  8. customdried under vacuum

출처 및 근거

ORD 기록
ord-68c24091559e4105b47871d18043d828
출처 데이터셋
uspto-grants-2011_11
특허 번호
US08053454B2

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