Isopropanol → N'-[3-(2-fluoro-4-iodophenyl)-2,6-dioxo-1,2,3,6-tetrahydropyrimidin-4-yl]-N,N-dimethylformamidine

HRID 75673Notes

Reaction equation

HRID 75673 reaction equation
[NH2:1][C:2]1[N:7]([C:8]2[CH:13]=[CH:12][C:11]([I:14])=[CH:10][C:9]=2[F:15])[C:6](=[O:16])[NH:5][C:4](=[O:17])[CH:3]=1.[CH3:18][N:19]([CH3:22])[CH:20]=O.CN(C(OC)OC)C.C(O)(C)C>O>[F:15][C:9]1[CH:10]=[C:11]([I:14])[CH:12]=[CH:13][C:8]=1[N:7]1[C:2]([N:1]=[CH:18][N:19]([CH3:22])[CH3:20])=[CH:3][C:4](=[O:17])[NH:5][C:6]1=[O:16]

Participants

6

Reactant 4

HCID 3776IsopropanolHCID 6228DimethylformamideHCID 78373Dimethylformamide dimethyl acetalHCID 597173056-amino-1-(2-fluoro-4-iodophenyl)-1H-pyrimidine-2,4-dione

Product 1

HCID 67025000N'-[3-(2-fluoro-4-iodophenyl)-2,6-dioxo-1,2,3,6-tetrahydropyrimidin-4-yl]-N,N-dimethylformamidineYield 67.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture (21.8 g) of 6-amino-1-(2-fluoro-4-iodophenyl)-1H-pyrimidine-2,4-dione 80 and 78 was added N,N-dimethylformamide (42.0 ml) and N,N-dimethylformamidedimethylacetal (21.0 ml) and the mixture was stirred at room temperature for 4.5 hrs. With stirring at room temperature, isopropyl alcohol (20.0 ml) was added, and water (100 ml) was added dropwise. The mixture was stirred at room temperature for 45 min, and the precipitated crystals were collected by filtration, washed with water and dried to give N′-[3-(2-fluoro-4-iodophenyl)-2,6-dioxo-1,2,3,6-tetrahydropyrimidin-4-yl]-N,N-dimethylformamidine 81 (21.7 g, yield 67.7% from 78) as colorless crystals.

Workup

  1. stirringWith stirring at room temperature
  2. stirringThe mixture was stirred at room temperature for 45 min
  3. filtrationthe precipitated crystals were collected by filtration
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-c0891eea23054e268d7ef8d2f9f9a520
Source dataset
uspto-grants-2014_09
Patent number
US08835443B2

Reaction notes

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