Acetic Acid → 6-Bromopyrazolo[1,5-a]pyrimidine-3-carboxylic acid

HRID 418284

반응식

HRID 418284 반응식
[NH2:1][C:2]1[NH:6][N:5]=[CH:4][C:3]=1[C:7]([O:9]CC)=[O:8].[OH-].[Na+].C(O)(=O)C.[Br:18][CH:19]([CH:22]=O)[CH:20]=O>C(O)C>[Br:18][C:19]1[CH:20]=[N:1][C:2]2[N:6]([N:5]=[CH:4][C:3]=2[C:7]([OH:9])=[O:8])[CH:22]=1

참가 물질

6

반응물 4

HCID 176Acetic AcidHCID 14798Sodium Hydroxide2회HCID 749452-BromopropanedialHCID 81472ethyl 3-amino-1H-pyrazole-4-carboxylate

생성물 1

HCID 252207936-Bromopyrazolo[1,5-a]pyrimidine-3-carboxylic acid수율 50.9%

시약·촉매·용매 1

HCID 702Ethanol용매2회

반응 조건

온도
70 °C

실험 절차

A solution of ethyl 5-amino-1H-pyrazole-4-carboxylate (2 g, 12.89 mmol) and sodium hydroxide (19.34 mL, 38.7 mmol) (aqueous, 2M) in ethanol (30 mL) was heated at 80° C. overnight. The reaction mixture was concentrated in vacuo to give a crude mixture of carboxylate and sodium hydroxide. The crude mixture was dissolved in ethanol (4 mL) and acetic acid (14 mL, 245 mmol). Whilst stirring the mixture, bromomalonaldehyde (1.947 g, 12.90 mmol) was added and then the mixture heated to 70° C. for 1 h. The reaction mixture was allowed to cool and the precipitate was filtered and washed with ethanol. The solid product was dried in a vacuum oven to give the title compound (1.589 g).

후처리

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customto give a crude
  3. additionwas added
  4. temperatureto cool
  5. filtrationthe precipitate was filtered
  6. washwashed with ethanol
  7. customThe solid product was dried in a vacuum oven

출처 및 근거

ORD 기록
ord-5249bd5d12a84c86b40b10be0ee46e27
출처 데이터셋
uspto-grants-2012_01
특허 번호
US08093249B2

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