Ammonium Chloride → HCID 59639533、化合物

HRID 2252897ノート

反応式

HRID 2252897 の反応式
C1[O:18][CH2:17][CH2:16]OCCOCCOCCOCCOC1.COC(CP(=O)(OCC(F)(F)F)OCC(F)(F)F)=O.C[Si]([N-][Si](C)(C)C)(C)C.[K+].[NH2:48][C:49]1[C:54]([CH:55]=O)=[C:53]([C:57]2[CH:62]=[CH:61][CH:60]=[CH:59][C:58]=2[F:63])[N:52]=[C:51]([S:64][CH3:65])[N:50]=1.[NH4+].[Cl-]>C1(C)C=CC=CC=1.C1COCC1.CCOCC>[F:63][C:58]1[CH:59]=[CH:60][CH:61]=[CH:62][C:57]=1[C:53]1[C:54]2[CH:55]=[CH:16][C:17](=[O:18])[NH:48][C:49]=2[N:50]=[C:51]([S:64][CH3:65])[N:52]=1

参加物

9

反応物 5

HCID 25517Ammonium ChlorideHCID 2855718-Crown-6HCID 184894Nsc 634137HCID 3251421Potassium bis(trimethylsilyl)amideHCID 9856557HCID 9856557、化合物

生成物 1

HCID 59639533HCID 59639533、化合物収率 108.8%

試薬・触媒・溶媒 3

HCID 1140Toluene溶媒HCID 3283Diethyl Ether溶媒HCID 8028Tetrahydrofuran溶媒2 回

実験手順

A solution of 18-crown-6 (422 mg, 1.6 mmol, 5 eq) and bis(2,2,2-trifluoroethyl) (methoxycarbonylmethyl)phosphonate (81 uL, 0.38 mmol, 1.2 eq) in anhyd THF (20 mL) was cooled to −78°, potassium bis(trimethylsilyl)amide (0.96 mL, 0.48 mmol, 1.5 eq) as a 0.5 mol solution in toluene was added. This solution was stirred for additional 30 min at −78° and 4-amino-6-(2-fluoro-phenyl)-2-methylsulfanyl-pyrimidine-5-carbaldehyde (85 mg, 0.32 mmol) in dry THF (1 mL) was added dropwise. The reaction mixture was then stirred for 8 h at −78° and warmed to 23°, and stirred 16 h. Saturated aq NH4Cl (5 mL), followed by Et2O (20 mL), was added. The layers were separated. The organic layer was washed with satd aq NaCl, dried (MgSO4), filtered and solvent was evaporated. The yellow residue was purified by Flash chromatography to afford 100 mg (91% yield) of 4-(2-fluoro-phenyl)-2-methylsulfanyl-8H-pyrido[2,3-d]pyrimidin-7-one. 1H-NMR δ 2.62 (s, 3H), 6.55 (d, 1H, J=9.9 Hz), 7.26 (m, 3H), 7.52 (m, 2H), 8.99 (br s, 1H). LC MS (m/e)=288 (MH+). Rt=1.75 min.

後処理

  1. stirringThe reaction mixture was then stirred for 8 h at −78°
  2. temperaturewarmed to 23°
  3. stirringstirred 16 h
  4. additionwas added
  5. customThe layers were separated
  6. washThe organic layer was washed with satd aq NaCl
  7. dry with materialdried (MgSO4)
  8. filtrationfiltered
  9. customsolvent was evaporated
  10. customThe yellow residue was purified by Flash chromatography

出典と根拠

ORDレコード
ord-bb4e5643582d4b5ebb130aef8fe286ce
出典データセット
uspto-grants-2008_01
特許番号
US07323472B2

反応ノート

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