Cesium carbonate → HCID 67328492, compound

HRID 2092586Notes

Reaction equation

HRID 2092586 reaction equation
C1(P(C2C=CC=CC=2)C2C3OC4C(=CC=CC=4P(C4C=CC=CC=4)C4C=CC=CC=4)C(C)(C)C=3C=CC=2)C=CC=CC=1.Br[C:44]1[CH:45]=[N:46][CH:47]=[N:48][CH:49]=1.[CH3:50][C:51]1[CH:56]=[CH:55][C:54]([N+:57]([O-:59])=[O:58])=[CH:53][C:52]=1[N:60]1[CH2:70][CH2:69][C:63]2[N:64]=[C:65]([NH2:68])[N:66]=[CH:67][C:62]=2[CH2:61]1.C(=O)([O-])[O-].[Cs+].[Cs+]>O1CCOCC1>[CH3:50][C:51]1[CH:56]=[CH:55][C:54]([N+:57]([O-:59])=[O:58])=[CH:53][C:52]=1[N:60]1[CH2:70][CH2:69][C:63]2[N:64]=[C:65]([NH:68][C:44]3[CH:45]=[N:46][CH:47]=[N:48][CH:49]=3)[N:66]=[CH:67][C:62]=2[CH2:61]1

Participants

6

Reactant 4

HCID 10796Cesium carbonateHCID 783445-BromopyrimidineHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 67328260HCID 67328260, compound

Product 1

HCID 67328492HCID 67328492, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of 4,5 Bis(diphenyl-phosphino)-9,9-dimethylxanthene [xanthopos](8.6 mg, 0.01488 mmol) and Tris(dibenzylideneacetone)di-palladium(0)[Pd2(dba)3](6.81 mg, 0.00744 mmol) in dry 1,4-dioxane (5 ml) was stirred vigorously and nitrogen was bubbled through the suspension for 30 minutes. 5-Bromo pyrimidine (19.7 mg, 0.1247 mmol), 6-(2-Methyl-5-nitro-phenyl)-5,6,7,8-tetrahydro-pyrido[4,3-d]pyrimidin-2-ylamine (35.57 mg, 0.1247 mmol) and dry cesium carbonate (100 mg, 0.31 mmol) was added. Nitrogen was bubbled through for another 30 minutes; the mixture was allowed to reflux overnight. The mixture was cooled, diluted with ethylacetate, water was added and the layers were separated. The aqueous layer was extracted with ethyl acetate and the two organic extracts were combined. The organics were washed with brine, then dried (sodium sulfate), filtered and concentrated under vacuum. Further purification by silica gel chromatography using 5-10% ethyl acetate/hexane as eluent provided [6-(2-Methyl-5-nitro-phenyl)-5,6,7,8-tetrahydro-pyrido[4,3-d]pyrimidin-2-yl]-pyrimidin-5-yl-amine [15] as a yellow solid [Yield: 9.75 mg, 21.7%]

Workup

  1. customnitrogen was bubbled through the suspension for 30 minutes
  2. customNitrogen was bubbled through for another 30 minutes
  3. temperatureto reflux overnight
  4. temperatureThe mixture was cooled
  5. additiondiluted with ethylacetate, water
  6. additionwas added
  7. customthe layers were separated
  8. extractionThe aqueous layer was extracted with ethyl acetate
  9. washThe organics were washed with brine
  10. dry with materialdried (sodium sulfate)
  11. filtrationfiltered
  12. concentrationconcentrated under vacuum
  13. customFurther purification by silica gel chromatography

Sources & evidence

ORD record
ord-7c1b99ae7b3a45bdb57466ee6a962716
Source dataset
uspto-grants-2013_05
Patent number
US08440679B2

Reaction notes

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