(R)-3-[2-(tert-butyl-dimethyl-silanyloxy)-1-methyl-ethyl]-1-(2,4-dichloro-pyrimidin-5-yl-methyl)-1-(4-ethyl-phenyl)-urea → (R)-1-[2-(tert-butyl-dimethyl-silanyloxy)-1-methyl-ethyl]-7-chloro-3-(4-ethyl-phenyl)-3,4-dihydro-1H-pyrimido[4,5-d]pyrimidin-2-one

HRID 1243224ノート

反応式

HRID 1243224 の反応式
[C:1]([Si:5]([CH3:32])([CH3:31])[O:6][CH2:7][C@H:8]([NH:10][C:11](=[O:30])[N:12]([CH2:21][C:22]1[C:23](Cl)=[N:24][C:25]([Cl:28])=[N:26][CH:27]=1)[C:13]1[CH:18]=[CH:17][C:16]([CH2:19][CH3:20])=[CH:15][CH:14]=1)[CH3:9])([CH3:4])([CH3:3])[CH3:2].CC(C)([O-])C.[K+]>O1CCCC1>[C:1]([Si:5]([CH3:31])([CH3:32])[O:6][CH2:7][C@H:8]([N:10]1[C:23]2=[N:24][C:25]([Cl:28])=[N:26][CH:27]=[C:22]2[CH2:21][N:12]([C:13]2[CH:18]=[CH:17][C:16]([CH2:19][CH3:20])=[CH:15][CH:14]=2)[C:11]1=[O:30])[CH3:9])([CH3:3])([CH3:2])[CH3:4]

参加物

4

反応物 2

HCID 11488861(R)-3-[2-(tert-butyl-dimethyl-silanyloxy)-1-methyl-ethyl]-1-(2,4-dichloro-pyrimidin-5-yl-methyl)-1-(4-ethyl-phenyl)-ureaHCID 23665647Potassium tert-butoxide

生成物 1

HCID 11271157(R)-1-[2-(tert-butyl-dimethyl-silanyloxy)-1-methyl-ethyl]-7-chloro-3-(4-ethyl-phenyl)-3,4-dihydro-1H-pyrimido[4,5-d]pyrimidin-2-one

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

A solution of (R)-3-[2-(tert-butyl-dimethyl-silanyloxy)-1-methyl-ethyl]-1-(2,4-dichloro-pyrimidin-5-yl-methyl)-1-(4-ethyl-phenyl)-urea (380 mg, 0.76 mmol) (from Example 38d supra) in tetrahydrofuran (10 mL) was treated at room temperature with potassium tert-butoxide (160 mg, 1.14 mmol) (Aldrich). The mixture was stirred at room temperature for 1.5 hours. The reaction mixture was quenched with saturated aqueous sodium bicarbonate solution and extracted with ethyl acetate. The combined organic layers were washed with brine, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The residue (395 mg, yellow oil) was purified by flash chromatography to give (R)-1-[2-(tert-butyl-dimethyl-silanyloxy)-1-methyl-ethyl]-7-chloro-3-(4-ethyl-phenyl)-3,4-dihydro-1H-pyrimido[4,5-d]pyrimidin-2-one as a colorless oil. (Yield 102 mg, 30%).

後処理

  1. customThe reaction mixture was quenched with saturated aqueous sodium bicarbonate solution
  2. extractionextracted with ethyl acetate
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue (395 mg, yellow oil) was purified by flash chromatography

出典と根拠

ORDレコード
ord-9efb35800a284290b1f04559d72d9eca
出典データセット
uspto-grants-2006_10
特許番号
US07115740B2

反応ノート

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