Water → (8S)-9-(2-chlorobenzyl)-2-(morpholin-4-yl)-8-(trifluoro-methyl)-6,7,8,9-tetrahydro-4H-pyrimido[1,2-a]pyrimidin-4-one

HRID 80614노트

반응식

HRID 80614 반응식
C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[Cl:15].[N:16]1([C:22]2[N:23]=[C:24]3[NH:32][C@H:31]([C:33]([F:36])([F:35])[F:34])[CH2:30][CH2:29][N:25]3[C:26](=[O:28])[CH:27]=2)[CH2:21][CH2:20][O:19][CH2:18][CH2:17]1.O>CN(C)C=O>[Cl:15][C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=1[CH2:8][N:32]1[C:24]2=[N:23][C:22]([N:16]3[CH2:21][CH2:20][O:19][CH2:18][CH2:17]3)=[CH:27][C:26](=[O:28])[N:25]2[CH2:29][CH2:30][C@H:31]1[C:33]([F:34])([F:35])[F:36]

참가 물질

6

반응물 4

HCID 962WaterHCID 10796Cesium carbonateHCID 11905alpha-Bromo-o-chlorotolueneHCID 136238743(S)-8-(Morpholin-4-yl)-2-(trifluoromethyl)-1,2,3,4-tetrahydropyrimido[1,2-a]pyrimidin-6-one

생성물 1

HCID 49854196(8S)-9-(2-chlorobenzyl)-2-(morpholin-4-yl)-8-(trifluoro-methyl)-6,7,8,9-tetrahydro-4H-pyrimido[1,2-a]pyrimidin-4-one

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

214 mg of caesium carbonate and 74 mg of 1-(bromomethyl)-2-chlorobenzene are added to a solution of 100 mg of (8S)-2-(morpholin-4-yl)-8-(trifluoromethyl)-6,7,8,9-tetrahydro-4H-pyrimido[1,2-a]pyrimidin-4-one (Example 1e) in 2 ml of dimethylformamide. After 16 hours at a temperature in the region of 20° C., the reaction medium is run into water. The organic phase is separated and the aqueous phase is extracted with ethyl acetate. The combined organic phases are concentrated to dryness under reduced pressure. The residue is purified by preparative HPLC/MS (Method C). After evaporation of the acetonitrile and lyophilization, 94 mg of (8S)-9-(2-chloro-benzyl)-2-(morpholin-4-yl)-8-(trifluoromethyl)-6,7,8,9-tetrahydro-4H-pyrimido[1,2-a]pyrimidin-4-one are obtained in the form of an oil, the characteristics of which are the following:

후처리

  1. customThe organic phase is separated
  2. extractionthe aqueous phase is extracted with ethyl acetate
  3. concentrationThe combined organic phases are concentrated to dryness under reduced pressure
  4. customThe residue is purified by preparative HPLC/MS (Method C)
  5. customAfter evaporation of the acetonitrile and lyophilization, 94 mg of (8S)-9-(2-chloro-benzyl)-2-(morpholin-4-yl)-8-(trifluoromethyl)-6,7,8,9-tetrahydro-4H-pyrimido[1,2-a]pyrimidin-4-one
  6. customare obtained in the form of an oil

출처 및 근거

ORD 기록
ord-59858c38fb89486182308dde46b4b38f
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08846670B2

반응 노트

불러오는 중…