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

HRID 80609
Notes
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Reaction equation

HRID 80609 reaction equation
C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH2:8][C:9]1[CH:14]=[CH:13][C:12]([F:15])=[CH:11][CH:10]=1.[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>C(#N)C>[F:15][C:12]1[CH:13]=[CH:14][C:9]([CH2:8][N:32]2[C:24]3=[N:23][C:22]([N:16]4[CH2:21][CH2:20][O:19][CH2:18][CH2:17]4)=[CH:27][C:26](=[O:28])[N:25]3[CH2:29][CH2:30][C@H:31]2[C:33]([F:34])([F:35])[F:36])=[CH:10][CH:11]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 680214-Fluorobenzyl bromideHCID 136238743(S)-8-(Morpholin-4-yl)-2-(trifluoromethyl)-1,2,3,4-tetrahydropyrimido[1,2-a]pyrimidin-6-one

Product 1

HCID 49854089(8S)-9-(4-fluorobenzyl)-2-(morpholin-4-yl)-8-(trifluoromethyl)-6,7,8,9-tetrahydro-4H-pyrimido[1,2-a]pyrimidin-4-one

Reagents, catalysts & solvents 1

HCID 6342
Acetonitrile
Solvent

Conditions

Temperature
80 °C

Procedure

0.536 g of caesium carbonate and 0.44 ml of 1-(bromomethyl)-4-fluorobenzene are added, under an argon atmosphere, to a solution of 300 mg of (S)-2-morpholin-4-yl-8-trifluoromethyl-6,7,8,9-tetrahydro-pyrimido[1,2-a]pyrimidin-4-one (Example 1e) in 3 ml of acetonitrile. The resulting mixture is then heated at 80° C. for 2 hours. The reaction mixture is then evaporated under reduced pressure and the residue obtained is then purified by silica chromatography (eluent: CH2Cl2/MeOH 98/02) so as to give 61 mg of (8S)-9-(4-fluorobenzyl)-2-(morpholin-4-yl)-8-(trifluoromethyl)-6,7,8,9-tetrahydro-4H-pyrimido[1,2-a]pyrimidin-4-one, in the form of a white solid, the characteristics of which are the following:

Workup

  1. customThe reaction mixture is then evaporated under reduced pressure
  2. customthe residue obtained
  3. customis then purified by silica chromatography (eluent: CH2Cl2/MeOH 98/02) so as

Sources & evidence

ORD record
ord-0b8badba5a1740e1967514ef0a45d91a
Source dataset
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08846670B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes