Isopropanol → (E)-N'-(1-Cyclopropyl-3-(2-fluoro-4-iodophenyl)-2,6-dioxo-1,2,3,6-tetrahydropyrimidin-4-yl)-N,N-dimethylformimidamide

HRID 75658Notes

Reaction equation

HRID 75658 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])[N:5]([CH:17]2[CH2:19][CH2:18]2)[C:4](=[O:20])[CH:3]=1.[CH3:21][N:22]([CH3:25])[CH:23]=O.COC(OC)N(C)C.C(O)(C)C>O>[CH:17]1([N:5]2[C:4](=[O:20])[CH:3]=[C:2]([N:1]=[CH:21][N:22]([CH3:25])[CH3:23])[N:7]([C:8]3[CH:13]=[CH:12][C:11]([I:14])=[CH:10][C:9]=3[F:15])[C:6]2=[O:16])[CH2:18][CH2:19]1

Participants

6

Reactant 4

HCID 3776IsopropanolHCID 6228DimethylformamideHCID 78373Dimethylformamide dimethyl acetalHCID 597171876-Amino-3-cyclopropyl-1-(2-fluoro-4-iodophenyl)pyrimidine-2,4(1H,3H)-dione

Product 1

HCID 67024888(E)-N'-(1-Cyclopropyl-3-(2-fluoro-4-iodophenyl)-2,6-dioxo-1,2,3,6-tetrahydropyrimidin-4-yl)-N,N-dimethylformimidamideYield 92%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Under a nitrogen atmosphere, to 6-amino-3-cyclopropyl-1-(2-fluoro-4-iodo-phenyl)-1H-pyrimidine-2,4-dione 75 (178 g) were added N,N-dimethylformamide (356 ml) and N,N-dimethylformamide dimethylacetal (178 ml), and the mixture was stirred at room temperature for 2 hrs. Isopropanol (178 ml) was added with stirring at room temperature, and water (1068 ml) was added dropwise. The mixture was stirred at room temperature for 2 hrs, and the precipitated crystals were collected by filtration and dried to give N′-[1-cyclopropyl-3-(2-fluoro-4-iodo-phenyl)-2,6-dioxo-1,2,3,6-tetrahydro-pyrimidin-4-yl]-N,N-dimethyl-formamidine 76 (188 g, yield 92%) as yellow crystals.

Workup

  1. stirringwith stirring at room temperature
  2. stirringThe mixture was stirred at room temperature for 2 hrs
  3. filtrationthe precipitated crystals were collected by filtration
  4. customdried

Sources & evidence

ORD record
ord-5e28ff4873334528b70c69661fc32e1b
Source dataset
uspto-grants-2014_09
Patent number
US08835443B2

Reaction notes

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