Cesium carbonate → HCID 59128642, compound

HRID 1991019Notes

Reaction equation

HRID 1991019 reaction equation
[CH:1]1([NH:6][C:7]2[C:12]([CH:13]=O)=[CH:11][N:10]=[C:9]([S:15][CH3:16])[N:8]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.C[O:18][C:19](=O)[CH2:20][C:21]1[CH:26]=[C:25]([C:27]2[O:28][C:29]([CH2:32][CH:33]([CH3:35])[CH3:34])=[N:30][N:31]=2)[CH:24]=[CH:23][C:22]=1[CH3:36].C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C)C(=O)C>[CH:1]1([N:6]2[C:7]3[N:8]=[C:9]([S:15][CH3:16])[N:10]=[CH:11][C:12]=3[CH:13]=[C:20]([C:21]3[CH:26]=[C:25]([C:27]4[O:28][C:29]([CH2:32][CH:33]([CH3:35])[CH3:34])=[N:30][N:31]=4)[CH:24]=[CH:23][C:22]=3[CH3:36])[C:19]2=[O:18])[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 107998964-(Cyclopentylamino)-2-(methylthio)pyrimidine-5-carbaldehydeHCID 59128635HCID 59128635, compound

Product 1

HCID 59128642HCID 59128642, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 4-cyclopentylamino-2-methylsulfanyl-pyrimidine-5-carbaldehyde (0.05 g, 0.22 mmol, from Preparation 4), [5-(5-isobutyl-[1,3,4]oxadiazol-2-yl)-2-methyl-phenyl]-acetic acid methyl ester (0.06 g, 0.21 mmol) and cesium carbonate (0.14 g, 0.43 mmol) in N,N-dimethylacetamide (4 mL) was heated in a microwave reactor at 100° C. for 3.5 hours. The reaction mixture was cooled and partitioned between ethyl acetate and water. The combined organic phase was washed with water and brine, dried (magnesium sulfate), filtered and concentrated under reduced pressure. The residue was purified by flash chromatography eluting with 30% ethyl acetate in hexanes to give 8-cyclopentyl-6-{5-(5-isobutyl-[1,3,4]oxadiazol-2-yl)-2-methyl-phenyl}-2-methylsulfanyl-8H-pyrido[2,3-d]pyrimidin-7-one (Yield: 0.04 g, 40%).

Workup

  1. temperatureThe reaction mixture was cooled
  2. custompartitioned between ethyl acetate and water
  3. washThe combined organic phase was washed with water and brine
  4. dry with materialdried (magnesium sulfate)
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by flash chromatography
  8. washeluting with 30% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-80da3bc6d50f4836bbfb1b46547e4107
Source dataset
uspto-grants-2010_01
Patent number
US07645764B2

Reaction notes

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