Dimethylformamide → N'-(5-fluoro-2-methylsulfanylpyrimidin-4-yl)-N,N-dimethylformamidine

HRID 1403178Notes

Reaction equation

HRID 1403178 reaction equation
[F:1][C:2]1[C:3]([NH2:10])=[N:4][C:5]([S:8][CH3:9])=[N:6][CH:7]=1.[CH3:11][N:12]([CH3:15])[CH:13]=O>C(OCC)C>[F:1][C:2]1[C:3]([N:10]=[CH:11][N:12]([CH3:15])[CH3:13])=[N:4][C:5]([S:8][CH3:9])=[N:6][CH:7]=1

Participants

4

Reactant 2

HCID 6228DimethylformamideHCID 205933515-Fluoro-2-(methylthio)pyrimidin-4-amine

Product 1

HCID 58318932N'-(5-fluoro-2-methylsulfanylpyrimidin-4-yl)-N,N-dimethylformamidineYield 84%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a solution of 5-fluoro-2-methylsulfanylpyrimidin-4-ylamine (7.5 g, 47.1 mmol) in N,N-dimethylformamide (DMF; 18 mL) was added DMF-dimethylacetal (DMF-DMA; 8.42 g, 70.7 mmol), and the resulting solution was stirred under nitrogen (N2) for 4 h. The homogeneous solution was diluted with diethyl ether (Et2O; 500 mL), washed with H2O (5×100 mL), and the organic phase was dried over Na2SO4, filtered, and concentrated to a white solid. Recrystallization from hexane afforded N′-(5-fluoro-2-methylsulfanylpyrimidin-4-yl)-N,N-dimethylformamidine (8.47 g, 84%) as white needles: mp 75-77° C.; 1H NMR (400 MHz, CDCl3) δ 8.67 (s, 1H), 8.12 (d, J=3.1 Hz, 1H), 3.19 (s, 3H), 3.18 (s, 3H), 2.53 (s, 3H); CIMS m/z 214 ([M]+).

Workup

  1. washwashed with H2O (5×100 mL)
  2. dry with materialthe organic phase was dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated to a white solid
  5. customRecrystallization from hexane

Sources & evidence

ORD record
ord-0cb777d5fc4b401ba7efa6841c03dfec
Source dataset
uspto-grants-2014_12
Patent number
US08912207B2

Reaction notes

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