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Benzoyl chloride → (S)-9-benzoyl-2-morpholin-4-yl-8-trifluoromethyl-6,7,8,9-tetrahydropyrimido[1,2-a]pyrimidin-4-one

HRID 80610
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HRID 80610 반응식
[H-].[Na+].[C:3](Cl)(=[O:10])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[N:12]1([C:18]2[N:19]=[C:20]3[NH:28][C@H:27]([C:29]([F:32])([F:31])[F:30])[CH2:26][CH2:25][N:21]3[C:22](=[O:24])[CH:23]=2)[CH2:17][CH2:16][O:15][CH2:14][CH2:13]1.C(=O)(O)[O-].[Na+]>O1CCCC1.C(OCC)(=O)C>[C:3]([N:28]1[C:20]2=[N:19][C:18]([N:12]3[CH2:17][CH2:16][O:15][CH2:14][CH2:13]3)=[CH:23][C:22](=[O:24])[N:21]2[CH2:25][CH2:26][C@H:27]1[C:29]([F:30])([F:31])[F:32])(=[O:10])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1
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참가 물질

7

반응물 4

HCID 7412Benzoyl chlorideHCID 24758Sodium hydrideHCID 516892Sodium BicarbonateHCID 136238743(S)-8-(Morpholin-4-yl)-2-(trifluoromethyl)-1,2,3,4-tetrahydropyrimido[1,2-a]pyrimidin-6-one

생성물 1

HCID 49854090(S)-9-benzoyl-2-morpholin-4-yl-8-trifluoromethyl-6,7,8,9-tetrahydropyrimido[1,2-a]pyrimidin-4-one

시약·촉매·용매 2

HCID 8028
Tetrahydrofuran
용매
HCID 8857Ethyl Acetate용매

실험 절차

35.7 mg of sodium hydride and then, after 10 minutes of stirring, 0.135 ml de of benzoyl chloride are added, under an argon atmosphere, to a solution of 300 mg of (S)-2-morpholin-4-yl-8-trifluoromethyl-6,7,8,9-tetrahydropyrimido[1,2-a]pyrimidin-4-one (Example 1e) in 3 ml of tetrahydrofuran. After stirring for six hours at ambient temperature, a saturated solution of sodium bicarbonate and ethyl acetate are added to the reaction mixture. The organic phase is separated and then successively washed with a saturated solution of sodium chloride, dried over magnesium sulphate, filtered and concentrated under reduced pressure. The residue obtained is purified by silica chromatography (eluent: CH2Cl2) so as to give 74 mg of (S)-9-benzoyl-2-morpholin-4-yl-8-trifluoromethyl-6,7,8,9-tetrahydropyrimido[1,2-a]pyrimidin-4-one, in the form of a white solid, the characteristics of which are the following:

후처리

  1. customThe organic phase is separated
  2. washsuccessively washed with a saturated solution of sodium chloride
  3. dry with materialdried over magnesium sulphate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue obtained
  7. customis purified by silica chromatography (eluent: CH2Cl2) so as

출처 및 근거

ORD 기록
ord-66222c9585074824a8d726bdf81f9c07
출처 데이터셋
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08846670B2

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