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Diiodomethane → 2-[1-(Cyclopentylmethyl)-5-fluoro-1H-pyrazolo[3,4-b]pyridin-3-yl]-4-iodo-5,5-dimethyl-5,7-dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one

HRID 1529165
ノート
印刷プレビュー

反応式

HRID 1529165 の反応式
I[CH2:2][I:3].N(OCCC(C)C)=O.NC1[C:14]2[C:37]([CH3:39])([CH3:38])[C:36](=[O:40])[NH:35][C:15]=2[N:16]=[C:17]([C:19]2[C:27]3[C:22](=[N:23][CH:24]=[C:25]([F:28])[CH:26]=3)[N:21]([CH2:29][CH:30]3[CH2:34][CH2:33][CH2:32][CH2:31]3)[N:20]=2)[N:18]=1>>[CH:30]1([CH2:29][N:21]2[C:22]3=[N:23][CH:24]=[C:25]([F:28])[CH:26]=[C:27]3[C:19]([C:17]3[N:18]=[C:2]([I:3])[C:14]4[C:37]([CH3:38])([CH3:39])[C:36](=[O:40])[NH:35][C:15]=4[N:16]=3)=[N:20]2)[CH2:34][CH2:33][CH2:32][CH2:31]1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

4

反応物 3

HCID 6346DiiodomethaneHCID 8053Isoamyl NitriteHCID 709796024-Amino-2-[1-(cyclopentyl methyl)-5-fluoro-1H-pyrazolo[3,4-b]pyridin-3-yl]-5,5-dimethyl-5,7-dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one

生成物 1

HCID 867151712-[1-(Cyclopentylmethyl)-5-fluoro-1H-pyrazolo[3,4-b]pyridin-3-yl]-4-iodo-5,5-dimethyl-5,7-dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one

反応条件

温度
85 °C

実験手順

40.549 g (151.398 mmol) of diiodomethane and 4.420 g (37.738 mmol) of isopentyl nitrite were added to 711 mg (1.799 mmol) of 4-amino-2-[1-(cyclopentylmethyl)-5-fluoro-1H-pyrazolo[3,4-b]pyridin-3-yl]-5,5-dimethyl-5,7-dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one. The mixture was stirred at 85° C. for 8 h. After cooling, the mixture was filtered, and the filtrate was diluted with cyclohexane and sucked through silica gel. The silica gel was washed with cyclohexane and the product was eluted with dichloromethane/methanol (v/v=50:2). The collected fractions were concentrated on a rotary evaporator, taken up in 20 ml of ethyl acetate and 5 ml of isopropanol, filtered and concentrated again. The residue was triturated with 5 ml of isopropanol. The solid was filtered off with suction and dried under high vacuum. This gave 230 mg (purity 92%, 23% of theory) of the target compound.

後処理

  1. temperatureAfter cooling
  2. filtrationthe mixture was filtered
  3. additionthe filtrate was diluted with cyclohexane
  4. washThe silica gel was washed with cyclohexane
  5. washthe product was eluted with dichloromethane/methanol (v/v=50:2)
  6. concentrationThe collected fractions were concentrated on a rotary evaporator
  7. filtration5 ml of isopropanol, filtered
  8. concentrationconcentrated again
  9. customThe residue was triturated with 5 ml of isopropanol
  10. filtrationThe solid was filtered off with suction
  11. customdried under high vacuum

出典と根拠

ORDレコード
ord-05e698dc80b44fb5b5713c63144a6c70
出典データセット
uspto-grants-2015_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09090610B2

反応ノート

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