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

HRID 1091696ノート

反応式

HRID 1091696 の反応式
[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

参加物

7

反応物 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

生成物 1

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

試薬・触媒・溶媒 4

HCID 23994Zinc触媒HCID 702Ethanol溶媒HCID 3283Diethyl Ether溶媒HCID 8900Heptane溶媒

実験手順

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%)

後処理

  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

出典と根拠

ORDレコード
ord-7a0293a2215a435eb9fb4d46ff352d2b
出典データセット
uspto-grants-2012_03
特許番号
US08129397B2

反応ノート

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