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

HRID 2408344Notes

Reaction equation

HRID 2408344 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 (8S)-2-chloro-8-(trifluoromethyl)-6,7,8,9-tetrahydro-4H-pyrimido[1,2-a]pyrimidin-4-one and of 15 mL of morpholine is heated to 80° C. After one hour and a half of heating and after monitoring with LC/MS, the reaction is completed. After cooling, the reaction mixture is concentrated under reduced pressure. On the obtained residue, 10 mL of cold water and 100 mL of ethyl acetate are added. The resulting organic phase is separated and then dried on magnesium sulfate, filtered and concentrated under reduced pressure in order to obtain 1.2 g of (8S)-2-(morpholin-4-yl)-8-(trifluoromethyl)-6,7,8,9-tetrahydro-4H-pyrimido[1,2-a]pyrimidin-4-one including the following characteristics:

Workup

  1. temperaturea half of heating
  2. temperatureAfter cooling
  3. concentrationthe reaction mixture is concentrated under reduced pressure
  4. additionOn the obtained residue, 10 mL of cold water and 100 mL of ethyl acetate are added
  5. customThe resulting organic phase is separated
  6. customdried on magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure in order

Sources & evidence

ORD record
ord-0e6e35b3b6044cf09bffe0576b52afea
Source dataset
uspto-grants-2014_08
Patent number
US08815853B2

Reaction notes

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