Hydroxyamine hydrochloride → 2-((4-(aminomethyl)-3-(trifluoromethyl)-1H-pyrazol-1-yl)methyl)-6-methylthieno[2,3-d]pyrimidin-4(3H)-one

HRID 1091696노트

반응식

HRID 1091696 반응식
[CH3:1][C:2]1[S:23][C:5]2[N:6]=[C:7]([CH2:11][N:12]3[CH:16]=[C:15]([CH:17]=O)[C:14]([C:19]([F:22])([F:21])[F:20])=[N:13]3)[NH:8][C:9](=[O:10])[C:4]=2[CH:3]=1.Cl.[NH2:25]O>C(O)C.CCOCC.CCCCCCC.[Zn]>[NH2:25][CH2:17][C:15]1[C:14]([C:19]([F:22])([F:21])[F:20])=[N:13][N:12]([CH2:11][C:7]2[NH:8][C:9](=[O:10])[C:4]3[CH:3]=[C:2]([CH3:1])[S:23][C:5]=3[N:6]=2)[CH:16]=1

참가 물질

7

반응물 2

HCID 443297Hydroxyamine hydrochlorideHCID 866303971-((6-Methyl-4-oxo-3,4-dihydrothieno[2,3-d]pyrimidin-2-yl)methyl)-3-(trifluoromethyl)-1H-pyrazole-4-carbaldehyde

생성물 1

HCID 665917222-((4-(aminomethyl)-3-(trifluoromethyl)-1H-pyrazol-1-yl)methyl)-6-methylthieno[2,3-d]pyrimidin-4(3H)-one수율 50.6%

시약·촉매·용매 4

HCID 23994Zinc촉매HCID 702Ethanol용매HCID 3283Diethyl Ether용매HCID 8900Heptane용매

실험 절차

A solution of 1-((6-methyl-4-oxo-3,4-dihydrothieno[2,3-d]pyrimidin-2-yl)methyl)-3-(trifluoromethyl)-1H-pyrazole-4-carbaldehyde (2.92 mmol, 1 g) and hydroxylamine hydrochloride (3.21 mmol, 0.223 g) in ethanol (7 mL) was heated to 80° C. and this temperature was maintained for 3 h. The reaction mixture was allowed to cool to room temperature & diluted with ether and heptane before the resulting precipitate was collected by filtration. The resulting solid was taken up in acetic acid (5 mL) and zinc (7.79 mmol, 0.510 g) and the whole was stirred at room temperature for 3 days with occassional agitation by sonication. The reaction mixture was filtered through celite and the pad washed with MeOH before the filtrate was concentrated under reduced pressure. The residue was dissolved in MeOH and applied to an SCX cartridge that had been equilibrated with the same solvent before being eluted with 2N NH3/MeOH to give a light yellow solid (271 mg, 0.79 mmol, 50.6%)

후처리

  1. temperaturethis temperature was maintained for 3 h
  2. filtrationwas collected by filtration
  3. filtrationThe reaction mixture was filtered through celite
  4. washthe pad washed with MeOH before the filtrate
  5. concentrationwas concentrated under reduced pressure
  6. dissolutionThe residue was dissolved in MeOH
  7. washbefore being eluted with 2N NH3/MeOH

출처 및 근거

ORD 기록
ord-7a0293a2215a435eb9fb4d46ff352d2b
출처 데이터셋
uspto-grants-2012_03
특허 번호
US08129397B2

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