Cesium carbonate → HCID 71136663, compound

HRID 1468821Notes

Reaction equation

HRID 1468821 reaction equation
[Br:1][C:2]1[CH:3]=[N:4][C:5]([N:8]2[CH2:13][CH2:12][CH:11]([C@H:14]3[CH2:16][C@H:15]3[CH2:17][O:18]CC3C=CC(S(C)(=O)=O)=CC=3)[CH2:10][CH2:9]2)=[N:6][CH:7]=1.C([O-])([O-])=O.[Cs+].[Cs+].BrC1C=NC(Cl)=NC=1>CN(C=O)C>[Br:1][C:2]1[CH:3]=[N:4][C:5]([N:8]2[CH2:13][CH2:12][CH:11]([C@H:14]3[CH2:16][C@H:15]3[CH2:17][OH:18])[CH2:10][CH2:9]2)=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 6066655-Bromo-2-chloropyrimidineHCID 86717778HCID 86717778, compound

Product 1

HCID 71136663HCID 71136663, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The product of step A (4.94 g, 19.6 mmol) was dissolved in DMF (40 mL), and Cs2CO3 (35 g, 107 mmol) and 5-bromo-2-chloropyrimidine (3.8 g, 19.6 mmol) were added. After stirring the mixture at RT for 5 hours, the mixture was partitioned between water and EtOAc. The aqueous layer was extracted with EtOAc. The combined organic layers were washed with water and brine. The organic layers were dried with Na2SO4 and concentrated in vacuo. The residue was purified via silica gel column chromatography (20/1, DCM/MeOH), yielding the title compound.

Workup

  1. customthe mixture was partitioned between water and EtOAc
  2. extractionThe aqueous layer was extracted with EtOAc
  3. washThe combined organic layers were washed with water and brine
  4. dry with materialThe organic layers were dried with Na2SO4
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified via silica gel column chromatography (20/1, DCM/MeOH)

Sources & evidence

ORD record
ord-b8c68bf7201444c781a736618f8cada9
Source dataset
uspto-grants-2015_04
Patent number
US09006228B2

Reaction notes

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