Cesium carbonate → HCID 68801871, compound

HRID 1348579Notes

Reaction equation

HRID 1348579 reaction equation
[C@H:1]12[CH2:7][CH:4]([NH:5][CH2:6]1)[CH2:3][N:2]2[C:8]1[N:13]([CH3:14])[C:12](=[O:15])[CH:11]=[C:10]([C:16]2[CH:21]=[CH:20][N:19]=[CH:18][CH:17]=2)[N:9]=1.Br[C:23]1[CH:24]=[N:25][CH:26]=[CH:27][CH:28]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>O1CCCC1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(P(C2C=CC=CC=2)C2C=CC3C(=CC=CC=3)C=2C2C3C(=CC=CC=3)C=CC=2P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH3:14][N:13]1[C:12](=[O:15])[CH:11]=[C:10]([C:16]2[CH:21]=[CH:20][N:19]=[CH:18][CH:17]=2)[N:9]=[C:8]1[N:2]1[CH2:3][CH:4]2[CH2:7][C@H:1]1[CH2:6][N:5]2[C:23]1[CH:24]=[N:25][CH:26]=[CH:27][CH:28]=1

Participants

7

Reactant 3

HCID 10796Cesium carbonateHCID 122863-BromopyridineHCID 68800475HCID 68800475, compound

Product 1

HCID 68801871HCID 68801871, compoundYield 46.5%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 634876Binap, (A+-)-CatalystHCID 8028TetrahydrofuranSolvent

Procedure

A mixture containing 0.2 g (0.71 mmol) of (1S)-2-(2,5-diaza-bicyclo[2.2.1]hept-2-yl)-3-methyl-6-pyridin-4-yl-3H-pyrimidin-4-one, 3.335 g (2.12 mmol) of 3-bromopyridine, 0.322 g (0.99 mmol) of cesium carbonate, 18 mg (0.028 mmol) of (+/−)-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl and 6 mg (0.028 mmol) of palladium(II) acetate in 100 ml of anhydrous tetrahydrofuran under argon atmosphere is stirred under reflux for 18 h. The mixture is filtered. Water is added to the filtrate and the resulting solution extracted with chloroform. The combined extracts are washed with saturated aqueous ammonium chloride and evaporated. The crude product is purified by chromatography on silica gel eluting with a mixture of dichloromethane/methanol in the proportions 100/0 to 95/5 to give 119 mg of pure compound as a solid.

Workup

  1. temperatureunder reflux for 18 h
  2. filtrationThe mixture is filtered
  3. additionWater is added to the filtrate
  4. extractionthe resulting solution extracted with chloroform
  5. washThe combined extracts are washed with saturated aqueous ammonium chloride
  6. customevaporated
  7. customThe crude product is purified by chromatography on silica gel eluting with a mixture of dichloromethane/methanol in the proportions 100/0 to 95/5

Sources & evidence

ORD record
ord-06626f87281e4a229453d0881a2f0ece
Source dataset
uspto-grants-2007_05
Patent number
US07211581B2

Reaction notes

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