Hydrochloric Acid → HCID 59299581, compound

HRID 2386646Notes

Reaction equation

HRID 2386646 reaction equation
[Cl:1][C:2]1[N:10](CC=C)[C:9]2[C:8](=[O:14])[N:7]([CH3:15])[C:6](=[O:16])[NH:5][C:4]=2[N:3]=1.C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH2:24][CH2:25][CH2:26][C:27]([F:30])([F:29])[F:28].N1CCOCC1.Cl>C1COCC1.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>[Cl:1][C:2]1[NH:10][C:9]2[C:8](=[O:14])[N:7]([CH3:15])[C:6](=[O:16])[N:5]([CH2:24][CH2:25][CH2:26][C:27]([F:30])([F:29])[F:28])[C:4]=2[N:3]=1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 8083MorpholineHCID 10796Cesium carbonateHCID 5210064-Bromo-1,1,1-trifluorobutaneHCID 59299531HCID 59299531, compound

Product 1

HCID 59299581HCID 59299581, compoundYield 10%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 8-chloro-1-methyl-7-(2-propen-1-yl)-3,7-dihydro-1H-purine-2,6-dione (0.048 g, 0.2 mmol) in THF (1 ml) was treated with caesium carbonate (0.78 g, 0.24 mmol) and 4-bromo-1,1,1-trifluorobutane (0.044 g, 0.25 mmol). The mixture was stirred at ambient temperature for 1 hour then heated at 50° C. for 4 hours and then cooled. The mixture was degassed by alternately applying vacuum and nitrogen pressure to the mixture and then treated with morpholine (0.17 ml, 2 mmol) and tetrakis(triphenylphosphine)palladium(0) (0.023 g, 0.02 mmol). After 2 hours the mixture was treated cautiously with 2M aqueous hydrochloric acid (2 ml) and the product extracted with chloroform (2×4 ml). The combined organics were evaporated and the product purified by reverse-phase mass directed HPLC to afford the title compound 6.2 mg (10%); NMR; δH (400 MHz, d6-DMSO); 1.84-1.92 (m, 2H), 2.28-2.35 (m, 2H), 3.22 (s, 3H), 3.99-4.03 (m, 2H) 14.31 (br.s, 1H); m/z 311.2 [MH+].

Workup

  1. temperaturethen heated at 50° C. for 4 hours
  2. temperaturecooled
  3. customThe mixture was degassed
  4. extractionthe product extracted with chloroform (2×4 ml)
  5. customThe combined organics were evaporated
  6. customthe product purified by reverse-phase mass

Sources & evidence

ORD record
ord-71c03a738045405a85f3a6844d717ef3
Source dataset
uspto-grants-2012_09
Patent number
US08268839B2

Reaction notes

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