Phenylacetyl chloride → (8S)-2-(morpholin-4-yl)-9-(phenylacetyl)-8-(trifluoromethyl)-6,7,8,9-tetrahydro-4H-pyrimido[1,2-a]pyrimidin-4-one

HRID 80630Notes

Reaction equation

HRID 80630 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.[H-].[Na+].[C:24]1([CH2:30][C:31](Cl)=[O:32])[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.C(Cl)Cl.CO>O1CCCC1.C(Cl)Cl.CCOC(C)=O>[N:1]1([C:7]2[N:8]=[C:9]3[N:17]([C:31](=[O:32])[CH2:30][C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=4)[C@H:16]([C:18]([F:20])([F:21])[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

Participants

7

Reactant 4

HCID 7679Phenylacetyl chlorideHCID 24758Sodium hydrideHCID 21226129Dichloromethane methanolHCID 136238743(S)-8-(Morpholin-4-yl)-2-(trifluoromethyl)-1,2,3,4-tetrahydropyrimido[1,2-a]pyrimidin-6-one

Product 1

HCID 49854609(8S)-2-(morpholin-4-yl)-9-(phenylacetyl)-8-(trifluoromethyl)-6,7,8,9-tetrahydro-4H-pyrimido[1,2-a]pyrimidin-4-oneYield 2.9%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 21226138Dichloromethane ethylacetateSolvent

Procedure

The product is prepared according to the procedure described in Example 18, using 300 mg of (8S)-2-morpholin-4-yl-8-trifluoromethyl-6,7,8,9-tetrahydropyrimido[1,2-a]pyrimidin-4-one (Example 1e), 47 mg of sodium hydride and 152 mg of phenylacetyl chloride in 4 ml of tetrahydrofuran. After two successive purifications by silica chromatography (eluent: CH2Cl2/MeOH; gradient of 100/0 to 98/02 then CH2Cl2/EtOAc 95/05), 12 mg of (8S)-2-(morpholin-4-yl)-9-(phenylacetyl)-8-(trifluoromethyl)-6,7,8,9-tetrahydro-4 H-pyrimido[1,2-a]pyrimidin-4-one are obtained in the form of a colourless lacquer, the characteristics of which are the following:

Workup

  1. customThe product is prepared

Sources & evidence

ORD record
ord-9d298615b7254d48be2628e8644e4725
Source dataset
uspto-grants-2014_09
Patent number
US08846670B2

Reaction notes

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