Morpholine → (S)-8-(Morpholin-4-yl)-2-(trifluoromethyl)-1,2,3,4-tetrahydropyrimido[1,2-a]pyrimidin-6-one

HRID 80604

Reaction equation

HRID 80604 reaction equation
Cl[C:2]1[N:3]=[C:4]2[NH:12][C@H:11]([C:13]([F:16])([F:15])[F:14])[CH2:10][CH2:9][N:5]2[C:6](=[O:8])[CH:7]=1.[NH:17]1[CH2:22][CH2:21][O:20][CH2:19][CH2:18]1>>[N:17]1([C:2]2[N:3]=[C:4]3[NH:12][C@H:11]([C:13]([F:16])([F:15])[F:14])[CH2:10][CH2:9][N:5]3[C:6](=[O:8])[CH:7]=2)[CH2:22][CH2:21][O:20][CH2:19][CH2:18]1

Participants

3

Reactant 2

HCID 8083MorpholineHCID 136238740(S)-8-chloro-2-(trifluoromethyl)-3,4-dihydro-1H-pyrimido[1,2-a]pyrimidin-6(2H)-one

Product 1

HCID 136238743(S)-8-(Morpholin-4-yl)-2-(trifluoromethyl)-1,2,3,4-tetrahydropyrimido[1,2-a]pyrimidin-6-one

Procedure

A mixture of 1 g of (S)-2-chloro-8-trifluoromethyl-6,7,8,9-tetrahydro-pyrimido[1,2-a]pyrimidin-4-one and of 15 ml of morpholine is heated at 80° C. After one and a half hours of heating and after verification by LC/MS, the reaction is complete. After cooling, the reaction mixture is concentrated under reduced pressure. 10 ml of cold water and 100 ml of ethyl acetate are added to the residue obtained. The resulting organic phase is separated and then dried over magnesium sulphate, filtered, and concentrated under reduced pressure so as to give 1.2 g of (S)-2-morpholin-4-yl-8-trifluoromethyl-6,7,8,9-tetrahydropyrimido[1,2-a]pyrimidin-4-one, the characteristics of which are the following:

Workup

  1. temperatureAfter one and a half hours of heating
  2. temperatureAfter cooling
  3. concentrationthe reaction mixture is concentrated under reduced pressure
  4. addition10 ml of cold water and 100 ml of ethyl acetate are added to the residue
  5. customobtained
  6. customThe resulting organic phase is separated
  7. dry with materialdried over magnesium sulphate
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure so as

Sources & evidence

ORD record
ord-98dcb3b1368642d2a805e9acb940d9a4
Source dataset
uspto-grants-2014_09
Patent number
US08846670B2

Linked notes

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