Cesium carbonate → HCID 118194317, compound

HRID 633744Notes

Reaction equation

HRID 633744 reaction equation
[Cl:1][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.C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH2:24][C:25](=[O:30])[C:26]([CH3:29])([CH3:28])[CH3:27]>C(#N)C>[Cl:1][C:2]1[N:3]=[C:4]2[N:12]([CH2:24][C:25](=[O:30])[C:26]([CH3:29])([CH3:28])[CH3:27])[C@H:11]([C:13]([F:14])([F:15])[F:16])[CH2:10][CH2:9][N:5]2[C:6](=[O:8])[CH:7]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 21642BromopinacoloneHCID 136238740(S)-8-chloro-2-(trifluoromethyl)-3,4-dihydro-1H-pyrimido[1,2-a]pyrimidin-6(2H)-one

Product 1

HCID 118194317HCID 118194317, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

150 mg (0.591 mmol) of (8S)-2-chloro-8-trifluoromethyl-6,7,8,9-tetrahydropyrimido[1,2-a]pyrimidin-4-one, 578.71 mg (1.77 mmol) of cesium carbonate, 99 μl (0.709 mmol) of 1-bromopinacolone and 10 mL of acetonitrile were used in the reaction. After purification by chromatography on silica gel (eluent A/B: DCM/MeOH, gradient A/B: t 0 min 0% B, t 12 min 4% B, t 15 min 4% B, t 30 min 10% B), 188 mg of (8S)-2-chloro-9-(3,3-dimethyl-2-oxobutyl)-8-trifluoromethyl-6,7,8,9-tetrahydropyrimido[1,2-a]pyrimidin-4-one were obtained, corresponding to the following characteristics:

Workup

  1. customAfter purification by chromatography on silica gel (eluent A/B: DCM/MeOH, gradient A/B: t 0 min 0% B, t 12 min 4% B, t 15 min 4% B, t 30 min 10% B), 188 mg of (8S)-2-chloro-9-(3,3-dimethyl-2-oxobutyl)-8-trifluoromethyl-6,7,8,9-tetrahydropyrimido[1,2-a]pyrimidin-4-one
  2. customwere obtained, corresponding to the following characteristics

Sources & evidence

ORD record
ord-33994a58e6bd434f844c84f0eda95054
Source dataset
uspto-grants-2016_04
Patent number
US09321790B2

Reaction notes

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