Cesium carbonate → (8S)-9-[(5-chloro-1-benzothiophen-3-yl)methyl]-2-(morpholin-4-yl)-8-(trifluoromethyl)-6,7,8,9-tetrahydro-4H-pyrimido[1,2-a]pyrimidin-4-one

HRID 80622Notes

Reaction equation

HRID 80622 reaction equation
[N:1]1([C:7]2[N:8]=[C:9]3[NH:17][C@H:16]([C:18]([F:21])([F:20])[F:19])[CH2:15][CH2:14][N:10]3[C:11](=[O:13])[CH:12]=2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH2:29][C:30]1[C:34]2[CH:35]=[C:36]([Cl:39])[CH:37]=[CH:38][C:33]=2[S:32][CH:31]=1>CN(C)C=O>[Cl:39][C:36]1[CH:37]=[CH:38][C:33]2[S:32][CH:31]=[C:30]([CH2:29][N:17]3[C:9]4=[N:8][C:7]([N:1]5[CH2:6][CH2:5][O:4][CH2:3][CH2:2]5)=[CH:12][C:11](=[O:13])[N:10]4[CH2:14][CH2:15][C@H:16]3[C:18]([F:20])([F:21])[F:19])[C:34]=2[CH:35]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 27798573-(Bromomethyl)-5-chloro-1-benzothiopheneHCID 136238743(S)-8-(Morpholin-4-yl)-2-(trifluoromethyl)-1,2,3,4-tetrahydropyrimido[1,2-a]pyrimidin-6-one

Product 1

HCID 49854301(8S)-9-[(5-chloro-1-benzothiophen-3-yl)methyl]-2-(morpholin-4-yl)-8-(trifluoromethyl)-6,7,8,9-tetrahydro-4H-pyrimido[1,2-a]pyrimidin-4-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The product is prepared according to the procedure described in Example 22, using 100 mg of (8S)-2-morpholin-4-yl-8-trifluoromethyl-6,7,8,9-tetrahydropyrimido[1,2-a]pyrimidin-4-one (Example 1e), 214 mg of caesium carbonate and 95 mg of 3-(bromomethyl)-5-chloro-1-benzothiophene in 2 ml of dimethylformamide. After purification by preparative HPLC/MS (Method C), 72 mg of (8S)-9-[(5-chloro-1-benzothiophen-3-yl)methyl]-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:

Workup

  1. customThe product is prepared
  2. customAfter purification by preparative HPLC/MS (Method C), 72 mg of (8S)-9-[(5-chloro-1-benzothiophen-3-yl)methyl]-2-(morpholin-4-yl)-8-(trifluoromethyl)-6,7,8,9-tetrahydro-4H-pyrimido[1,2-a]pyrimidin-4-one
  3. customare obtained in the form of an oil

Sources & evidence

ORD record
ord-db5b64d5cd5843a196ab5ef92c7d7025
Source dataset
uspto-grants-2014_09
Patent number
US08846670B2

Reaction notes

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