Cesium carbonate → N'-(5-fluoro-2-methoxymethoxypyrimidin-4-yl)-N,N-dimethyl-formamidine

HRID 705589Notes

Reaction equation

HRID 705589 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+].[CH3:20][O:21][CH2:22]Br>CN(C=O)C>[F:1][C:2]1[C:3]([N:9]=[CH:10][N:11]([CH3:13])[CH3:12])=[N:4][C:5]([O:8][CH2:20][O:21][CH3:22])=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 83093Bromomethyl methyl etherHCID 178484257HCID 178484257, compound

Product 1

HCID 57818652N'-(5-fluoro-2-methoxymethoxypyrimidin-4-yl)-N,N-dimethyl-formamidineYield 19%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

N′-(5-fluoro-2-hydroxypyrimidin-4-yl)-N,N-dimethylformamidine (100 mg, 0.54 mmol), cesium carbonate (196 mg, 0.60 mmol), and bromomethyl methyl ether (75 mg, 0.6 mmol) were shaken together in DMF (3 mL) at ambient temperature for 4 hours. The reaction mixture was partitioned between ethyl acetate and water, dried over magnesium sulfate, filtered and evaporated to yield a colorless oil which was placed directly onto a silica gel column and eluted with ethyl acetate in petroleum ether (0-80% gradient) to isolate 23 mg, 0.1 mmol (19%) of the title compound as a colorless oil: 1H NMR (CDCl3) δ 8.66 (s, 1H), 8.05 (d, J=2.6 Hz, 1H), 5.46 (s, 2H), 3.53 (s, 3H), 3.17 (s, 3H), 3.16 (s, 3H); HPLC-MS (ESI) m/z 229 (M+H)+.

Workup

  1. customThe reaction mixture was partitioned between ethyl acetate and water
  2. dry with materialdried over magnesium sulfate
  3. filtrationfiltered
  4. customevaporated
  5. customto yield a colorless oil which
  6. washeluted with ethyl acetate in petroleum ether (0-80% gradient)

Sources & evidence

ORD record
ord-03bcd53f109f4e009889f8c5ac02e7ff
Source dataset
uspto-grants-2015_11
Patent number
US09174970B2

Reaction notes

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