Ammonium Chloride → HCID 178462869、化合物

HRID 886808ノート

反応式

HRID 886808 の反応式
[NH2:1][C:2]1[N:3]=[C:4]([CH3:17])[C:5]2[CH:11]=[C:10]([C:12]#[CH:13])[C:9](=[O:14])[N:8]([CH2:15][CH3:16])[C:6]=2[N:7]=1.[N-:18]=[N+:19]=[N-:20].[Na+].[Cl-].[NH4+]>CN(C=O)C>[NH2:1][C:2]1[N:3]=[C:4]([CH3:17])[C:5]2[CH:11]=[C:10]([C:12]3[NH:20][N:19]=[N:18][CH:13]=3)[C:9](=[O:14])[N:8]([CH2:15][CH3:16])[C:6]=2[N:7]=1

参加物

5

反応物 3

HCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 576069672-amino-8-ethyl-6-ethynyl-4-methylpyrido[2,3-d]pyrimidin-7(8H)-one

生成物 1

HCID 178462869HCID 178462869、化合物収率 6%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
120 °C

実験手順

Anhydrous DMF (5.0 mL) was added to a flask charged with 2-amino-8-ethyl-6-ethynyl-4-methylpyrido[2,3-d]pyrimidin-7(8H)-one (0.204 g, 0.894 mmol), sodium azide (0.070 g, 1.07 mmol), and ammonium chloride (0.057 g, 1.07 mmol). The reaction was capped under nitrogen and heated to 120° C. After 48 h, the reaction was cooled to room temperature and concentrated in vacuo. The residue was purified on reverse phase HPLC (acetonitrile:water 0.1% TFA, 20-60% gradient). The fractions containing product were collected and concentrated to one half volume and poured into saturated NaHCO3 (50 mL). The aqueous phase was washed trice with ethyl acetate (50 mL) and dried over Na2SO4, filtered, and concentrated in vacuo. The residue was triturated with methylene chloride and ethyl acetate to afford 2-amino-8-ethyl-4-methyl-6-(1H-1,2,3-triazol-5-yl)pyrido[2,3-d]pyrimidin-7(8H)-one (14 mg, 6% yield) as a light yellow solid: 1H NMR (400 MHz, DMSO-d6): δ 8.55 (bs, 1H), 8.41 (bs, 1H), 7.32 (bs, 2H), 4.37 (q, J=7.2 Hz, 2H), 2.60 (s, 3H), 1.21 (t, J=7.2 Hz, 3H); MS (EI) for C12H13N7O: 272.0 (MH+).

後処理

  1. customThe reaction was capped under nitrogen
  2. temperaturethe reaction was cooled to room temperature
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified on reverse phase HPLC (acetonitrile:water 0.1% TFA, 20-60% gradient)
  5. additionThe fractions containing product
  6. customwere collected
  7. concentrationconcentrated to one half volume
  8. additionpoured into saturated NaHCO3 (50 mL)
  9. washThe aqueous phase was washed trice with ethyl acetate (50 mL)
  10. dry with materialdried over Na2SO4
  11. filtrationfiltered
  12. concentrationconcentrated in vacuo
  13. customThe residue was triturated with methylene chloride and ethyl acetate

出典と根拠

ORDレコード
ord-70a88a024eb2458e9443a9ab4857820f
出典データセット
uspto-grants-2012_08
特許番号
US08247408B2

反応ノート

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