Methyl Methanesulfonate → 5-Fluoro-4-imino-1-methyl-1,4-dihydropyrimidin-2-ol

HRID 1405981Notes

Reaction equation

HRID 1405981 reaction equation
[NH2:1][C:2]1[C:7]([F:8])=[CH:6][N:5]=[C:4]([OH:9])[N:3]=1.[C:10]([O-])([O-])=O.[K+].[K+].CS(OC)(=O)=O>CN(C=O)C>[NH2:1][C:2]1[C:7]([F:8])=[CH:6][N:5]([CH3:10])[C:4](=[O:9])[N:3]=1

Participants

5

Reactant 3

HCID 4156Methyl MethanesulfonateHCID 11430Potassium CarbonateHCID 178509007HCID 178509007, compound

Product 1

HCID 2553915-Fluoro-4-imino-1-methyl-1,4-dihydropyrimidin-2-olYield 37%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
85 °C

Procedure

A 25 mL screw-top vial was charged with 4-amino-5-fluoropyrimidin-2-ol (151.0 mg, 1.17 mmol), K2CO3 (289.2 mg, 2.09 mmol), 18C6 (278.6 mg, 0.901 mmol) and anhydrous DMF (10 mL). Methyl methanesulfonate (0.0814 mL, 0.961 mmol) was added, and the resulting mixture was agitated on a rotary shaker at 85° C. for 21 h. After cooling to room temperature, the crude material was concentrated in vacuo and purified by reverse phase column chromatography to afford 4-amino-5-fluoro-1-methylpyrimidin-2(1H)-one (61.9 mg, 37%) as a beige solid: mp 195° C. (dec.); 1H NMR (400 MHz, DMSO-d6) δ 7.94 (d, J=6.8 Hz, 1H), 7.52 (s, 1H), 7.32 (s, 1H), 3.18 (s, 3H); ESIMS m/z 144 ([M+H]+.

Workup

  1. temperatureAfter cooling to room temperature
  2. concentrationthe crude material was concentrated in vacuo
  3. custompurified by reverse phase column chromatography

Sources & evidence

ORD record
ord-e0af556e8aa44d3992904a8b0ea201fb
Source dataset
uspto-grants-2014_12
Patent number
US08916579B2

Reaction notes

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