Water → HCID 11568685, compound

HRID 908524Notes

Reaction equation

HRID 908524 reaction equation
[NH:1]1[CH:8]=[CH:7][C:5](=[O:6])[NH:4][C:2]1=[O:3].C([O-])([O-])=O.[Cs+].[Cs+].S(O[CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][NH:32][C:33]([C:46]1[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=1)([C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)(C1C=CC(C)=CC=1)(=O)=O.O>CN(C=O)C>[C:33]([NH:32][CH2:31][CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][N:1]1[CH:8]=[CH:7][C:5](=[O:6])[NH:4][C:2]1=[O:3])([C:40]1[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=1)([C:46]1[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=1)[C:34]1[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=1

Participants

6

Reactant 4

HCID 962WaterHCID 1174UracilHCID 10796Cesium carbonateHCID 11562580HCID 11562580, compound

Product 1

HCID 11568685HCID 11568685, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
40 °C

Procedure

Uracil (0.087 g, 0.776 mmol) was stirred with Cs2CO3 (0.169 g, 0.519 mmol) in DMF (4 mL) at room temperature for 1 h. A solution of O-tosyl-6-tritylaminohexanol (0.250 g, 0.487 mmol) in DMF (2 mL) was then added dropwise. The reaction mixture was heated at 40° C. for 64 h, left to cool to room temperature, poured into cold water (15 mL) and extracted with EtOAc (25 mL). The organic extracts were washed with brine (10 mL), dried over Na2SO4 and concentrated in vacuo. Further purification was carried out by flash column chromatography (ISOLUTE SI column) using a gradient elution of 20→50% EtOAc in hexane. The fractions with Rf=0.49 (10% CH3OH/CHCl3) gave the title compound slightly contaminated with DMF as a white solid (0.111 g, ca 50%). Remaining traces of DMF could be removed by recrystallisation from CH3OH or alternatively by water wash with a purification yield of 70-80%.

Workup

  1. waitleft
  2. temperatureto cool to room temperature
  3. extractionextracted with EtOAc (25 mL)
  4. washThe organic extracts were washed with brine (10 mL)
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated in vacuo
  7. customFurther purification
  8. washa gradient elution of 20→50% EtOAc in hexane

Sources & evidence

ORD record
ord-7701917f0b2e4a9b957ac0304e38008c
Source dataset
uspto-grants-2011_09
Patent number
US08017620B2

Reaction notes

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