Tetrahydrofuran → 4-chloro-1H-pyrazolo[3,4-d]pyrimidin-6-amine

HRID 1062818노트

반응식

HRID 1062818 반응식
[NH2:1][C:2]1[N:7]=[C:6]([Cl:8])[C:5]([CH:9]=O)=[C:4](Cl)[N:3]=1.C1COCC1.[NH2:17][NH2:18].O.NN>C(N(CC)CC)C>[Cl:8][C:6]1[N:7]=[C:2]([NH2:1])[N:3]=[C:4]2[NH:17][N:18]=[CH:9][C:5]=12

참가 물질

6

반응물 4

HCID 8028TetrahydrofuranHCID 9321Hydrazine2회HCID 24654Hydrazine hydrate (1:1)HCID 2655462-Amino-4,6-dichloropyrimidine-5-carboxaldehyde

생성물 1

HCID 117896254-chloro-1H-pyrazolo[3,4-d]pyrimidin-6-amine수율 85%

시약·촉매·용매 1

HCID 8471Triethylamine용매

실험 절차

To a mixture of 2-amino-4,6-dichloropyrimidine-5-carboxaldehyde (2) (150 g, 0.785 mol), THF (2.7 L) and triethylamine (125 ml) was added anhydrous hydrazine (25.5 ml in 600 ml of water) drop wise over 25 min. Alternatively, hydrazine monohydrate can be used instead of anhydrous hydrazine. The mixture was stirred for 1 h. The solids were filtered off and the filtrate was evaporated to remove about 80% of the THF. Water was added and the resulting precipitate was filtered and dried under vacuum. The solid was then dissolved in a minimum volume of hot DMF and precipitate by addition of water to provide 112 g (85% yield) of 4-chloro-6-aminopyrazolo[3,4-d]pyrimidine (3).

후처리

  1. filtrationThe solids were filtered off
  2. customthe filtrate was evaporated
  3. customto remove about 80% of the THF
  4. additionWater was added
  5. filtrationthe resulting precipitate was filtered
  6. customdried under vacuum
  7. dissolutionThe solid was then dissolved in a minimum volume of hot DMF and precipitate by addition of water

출처 및 근거

ORD 기록
ord-1d985ab335a5450282eabd5177ee6952
출처 데이터셋
uspto-grants-2005_11
특허 번호
US06962991B2

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