Dimethylformamide dimethyl acetal → N'-[5-Fluoro-1-(3-hydroxy-cyclopentyl)-2-oxo-1,2-dihydro-pyrimidin-4-yl]-N,N-dimethyl-formamidine

HRID 417828Notes

Reaction equation

HRID 417828 reaction equation
[NH2:1][C:2]1[C:7]([F:8])=[CH:6][N:5]([CH:9]2[CH2:13][CH2:12][CH:11]([OH:14])[CH2:10]2)[C:4](=[O:15])[N:3]=1.CO[CH:18](OC)[N:19]([CH3:21])[CH3:20]>CN(C)C=O>[F:8][C:7]1[C:2]([N:1]=[CH:18][N:19]([CH3:21])[CH3:20])=[N:3][C:4](=[O:15])[N:5]([CH:9]2[CH2:13][CH2:12][CH:11]([OH:14])[CH2:10]2)[CH:6]=1

Participants

4

Reactant 2

HCID 78373Dimethylformamide dimethyl acetalHCID 666491684-Amino-5-fluoro-1-(3-hydroxy-cyclopentyl)-1H-pyrimidin-2-one

Product 1

HCID 66649234N'-[5-Fluoro-1-(3-hydroxy-cyclopentyl)-2-oxo-1,2-dihydro-pyrimidin-4-yl]-N,N-dimethyl-formamidineYield 83%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 4-amino-5-fluoro-1-(3-hydroxy-cyclopentyl)-1H-pyrimidin-2-one (0.346 g, 1.62 mmol) in anhydrous dimethylformamide (3 mL) was treated with dimethylformamide dimethyl acetal (3 mL). The mixture was stirred at room temperature under nitrogen for 12 hours, concentrated in vacuo, loaded on silica gel, and chromatographed on silica gel (3×7 cm SiO2, 4:1 ethyl acetate/methanol) to afford N′-[5-Fluoro-1-(3-hydroxy-cyclopentyl)-2-oxo-1,2-dihydro-pyrimidin-4-yl]-N,N-dimethyl-formamidine 30 as a milky white oil (0.361 g, 83%).

Workup

  1. concentrationconcentrated in vacuo
  2. customchromatographed on silica gel (3×7 cm SiO2, 4:1 ethyl acetate/methanol)

Sources & evidence

ORD record
ord-0cc31c68a97940ac8f7574dd4986a74f
Source dataset
uspto-grants-2012_01
Patent number
US08093245B2

Reaction notes

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