Hydrochloric Acid → HCID 59395591, compound

HRID 1097712Notes

Reaction equation

HRID 1097712 reaction equation
[CH2:1]([N:5]1[C:13]2[N:12]=[C:11]([Cl:14])[N:10](CC=C)[C:9]=2[C:8](=[O:18])[NH:7][C:6]1=[O:19])[CH2:2][CH2:3][CH3:4].C(=O)([O-])[O-].[Cs+].[Cs+].Cl[CH2:27][CH2:28][CH2:29][C:30]1[O:31][C:32]([CH2:35][C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)=[N:33][N:34]=1.N1CCOCC1.Cl>CN(C=O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CCOC(C)=O>[CH2:1]([N:5]1[C:13]2[N:12]=[C:11]([Cl:14])[NH:10][C:9]=2[C:8](=[O:18])[N:7]([CH2:27][CH2:28][CH2:29][C:30]2[O:31][C:32]([CH2:35][C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=3)=[N:33][N:34]=2)[C:6]1=[O:19])[CH2:2][CH2:3][CH3:4]

Participants

9

Reactant 5

HCID 313Hydrochloric AcidHCID 8083MorpholineHCID 10796Cesium carbonateHCID 43513294HCID 43513294, compoundHCID 592995823-butyl-8-chloro-7-(2-propen-1-yl)-3,7-dihydro-1H-purine-2,6-dione

Product 1

HCID 59395591HCID 59395591, compoundYield 59.3%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 6228DimethylformamideSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
55 °C

Procedure

To 3-butyl-8-chloro-7-(2-propen-1-yl)-3,7-dihydro-1H-purine-2,6-dione (99 mg, 0.35 mmol) in dry DMF (2 ml) was added cesium carbonate (137 mg, 0.42 mmol) followed by a solution in dry DMF (1 ml) of 2-(3-chloropropyl)-5-(phenylmethyl)-1,3,4-oxadiazole (99 mg, 0.42 mmol). The mixture was stirred under nitrogen and heated at 55° C. for 2.5 h then stirred at room temperature overnight. The mixture was degassed by repeatedly evacuating and admitting nitrogen and then tetrakis(triphenylphosphine)palladium(0) (81 mg, 0.07 mmol) and morpholine (0.305 ml, 3.5 mmol) were added and stirring was continued for 5 h EtOAc and 2M HCl were added and the mixture stirred for 20 min then filtered. The organic phase was separated and evaporated, and the product was purified by aminopropyl SPE (5 g) washing with THF-MeOH (1:1) then with MeOH and eluting the acidic product with DCM-MeOH (1:1) containing 5% added AcOH. The product thus obtained was purified further by MDAP to yield the title compound (92 mg).

Workup

  1. stirringthen stirred at room temperature overnight
  2. customThe mixture was degassed
  3. customby repeatedly evacuating
  4. stirringstirring
  5. stirringthe mixture stirred for 20 min
  6. filtrationthen filtered
  7. customThe organic phase was separated
  8. customevaporated
  9. customthe product was purified by aminopropyl SPE (5 g)
  10. washwashing with THF-MeOH (1:1)
  11. washwith MeOH and eluting the acidic product with DCM-MeOH (1:1)
  12. additioncontaining 5%
  13. additionadded AcOH
  14. customThe product thus obtained
  15. customwas purified further by MDAP

Sources & evidence

ORD record
ord-1dbf0200f0da41a9a01e23089fb8ab87
Source dataset
uspto-grants-2012_03
Patent number
US08143264B2

Reaction notes

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