Cesium carbonate → HCID 58166473, compound

HRID 1405974Notes

Reaction equation

HRID 1405974 reaction equation
[F:1][C:2]1[C:3]([N:9]=[CH:10][N:11]([CH3:13])[CH3:12])=[N:4][C:5]([OH:8])=[N:6][CH:7]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[C:20]([O:26][CH2:27]Cl)(=[O:25])[C:21]([CH3:24])([CH3:23])[CH3:22]>CN(C=O)C>[CH3:12][N:11]([CH:10]=[N:9][C:3]1[C:2]([F:1])=[CH:7][N:6]([CH2:27][O:26][C:20](=[O:25])[C:21]([CH3:24])([CH3:23])[CH3:22])[C:5](=[O:8])[N:4]=1)[CH3:13]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 87885Chloromethyl pivalateHCID 178484257HCID 178484257, compound

Product 1

HCID 58166473HCID 58166473, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To DMF (3 mL) were added N′-(5-fluoro-2-hydroxypyrimidin-4-yl)-N,N-dimethylformamidine (100 mg, 0.54 mmol), cesium carbonate (196 mg, 0.6 mmol), and chloromethyl pivalate (90 mg, 0.6 mmol), and the mixture was shaken at room temperature for 16 h. The mixture was partitioned between EtOAc and H2O. The organic phase was dried over MgSO4, filtered, and evaporated. To the resultant crude oil Et2O (3.5 mL) was added and a precipitate formed which was collected by filtration. The title compound was isolated as a white solid (37 mg, 23%): mp 193-194° C.; 1H NMR (300 MHz, DMSO-d6) δ 8.67 (s, 1H), 8.07 (d, J=6.3 Hz, 1H), 5.60 (s, 2H), 3.22 (s, 3H), 3.09 (s, 3H), 1.11 (s, 9H); ESIMS m/z 299 ([M+H]+).

Workup

  1. customThe mixture was partitioned between EtOAc and H2O
  2. dry with materialThe organic phase was dried over MgSO4
  3. filtrationfiltered
  4. customevaporated
  5. additionTo the resultant crude oil Et2O (3.5 mL) was added
  6. customa precipitate formed which
  7. filtrationwas collected by filtration

Sources & evidence

ORD record
ord-68c3476f5ab842ed9565ed3896f2bad3
Source dataset
uspto-grants-2014_12
Patent number
US08916579B2

Reaction notes

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