Dichloromethane → (R)-8-Acetyl-2-(1-amino-ethyl)-3-(4-ethoxy-phenyl)-5,6,7,8-tetrahydro-3H-pyrido[2,3-d]pyrimidin-4-one

HRID 2223146ノート

反応式

HRID 2223146 の反応式
C(OC(=O)[NH:7][C@@H:8]([C:10]1[N:11]([C:24]2[CH:29]=[CH:28][C:27]([O:30][CH2:31][CH3:32])=[CH:26][CH:25]=2)[C:12](=[O:23])[C:13]2[CH2:19][CH2:18][CH2:17][N:16]([C:20](=[O:22])[CH3:21])[C:14]=2[N:15]=1)[CH3:9])(C)(C)C.ClCCl>FC(F)(F)C(O)=O>[C:20]([N:16]1[C:14]2[N:15]=[C:10]([C@H:8]([NH2:7])[CH3:9])[N:11]([C:24]3[CH:29]=[CH:28][C:27]([O:30][CH2:31][CH3:32])=[CH:26][CH:25]=3)[C:12](=[O:23])[C:13]=2[CH2:19][CH2:18][CH2:17]1)(=[O:22])[CH3:21]

参加物

4

反応物 2

HCID 6344DichloromethaneHCID 58617397(R)-{1-[8-Acetyl-3-(4-ethoxy-phenyl)-4-oxo-3,4,5,6,7,8-hexahydro-pyrido[2,3-d]pyrimidin-2-yl]-ethyl}-carbamic acid tert-butyl ester

生成物 1

HCID 58617407(R)-8-Acetyl-2-(1-amino-ethyl)-3-(4-ethoxy-phenyl)-5,6,7,8-tetrahydro-3H-pyrido[2,3-d]pyrimidin-4-one

試薬・触媒・溶媒 1

HCID 6422Trifluoroacetic acid溶媒

実験手順

D3 (268 mg, 0.59 mmol) was dissolved in 1:1 trifluoroacetic acid:dichloromethane (10 mL). The reaction stirred at room temperature for 30 min. The solvent was removed in vacuo, then 10% aqueous ammonium hydroxide was added until the aqueous pH=9. The aqueous layer was extracted three times with dichloromethane, then the combined organic layer was washed with saturated aqueous sodium bicarbonate and brine. It was dried over magnesium sulfate, filtered, and concentrated in vacuo, recovering 170 mg of D4. MS (MH+): 357.1. 1H NMR (400 MHz; CDCl3; T=298 K): δ 7.13 (ddd, 2H, J=18.9, 1.4, 1.1 Hz), 7.02 (ddd, 2H, J=9.0, 1.2, 0.8 Hz), 4.09 (dq, 2H, J=6.9, 1.2 Hz), 3.98-3.80 (ddq, 2H, J=62.6, 5.3, 1.0 Hz), 3.73 (dd, 1H, J=6.6, 1.2 Hz), 2.60 (s, 3H), 1.92 (m, 2H), 1.82 (broad s, 2H), 1.45 (ddd, 3H, J=8.3, 6.1, 1.3 Hz), 1.28-1.21 (m, 5H) ppm.

後処理

  1. customThe solvent was removed in vacuo
  2. addition10% aqueous ammonium hydroxide was added until the aqueous pH=9
  3. extractionThe aqueous layer was extracted three times with dichloromethane
  4. washthe combined organic layer was washed with saturated aqueous sodium bicarbonate and brine
  5. dry with materialIt was dried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customrecovering 170 mg of D4

出典と根拠

ORDレコード
ord-63b4fc9a6f684159bc2557e5bb0040df
出典データセット
uspto-grants-2008_05
特許番号
US07375102B2

反応ノート

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