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

HRID 75674Notes

Reaction equation

HRID 75674 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([I:8])[CH:5]=[CH:4][C:3]=1[N:9]1[C:14]([N:15]=[CH:16][N:17]([CH3:19])[CH3:18])=[CH:13][C:12](=[O:20])[NH:11][C:10]1=[O:21].N12CCCN=C1CCCCC2.[CH3:33][O:34][C:35]1[CH:42]=[CH:41][C:38]([CH2:39]Cl)=[CH:37][CH:36]=1.C(O)(C)C>CN(C)C=O.O>[F:1][C:2]1[CH:7]=[C:6]([I:8])[CH:5]=[CH:4][C:3]=1[N:9]1[C:14]([N:15]=[CH:16][N:17]([CH3:18])[CH3:19])=[CH:13][C:12](=[O:20])[N:11]([CH2:39][C:38]2[CH:41]=[CH:42][C:35]([O:34][CH3:33])=[CH:36][CH:37]=2)[C:10]1=[O:21]

Participants

7

Reactant 4

HCID 3776IsopropanolHCID 699934-Methyloxybenzyl chloride2×HCID 811841,8-Diazabicyclo(5.4.0)undec-7-ene2×HCID 67025000N'-[3-(2-fluoro-4-iodophenyl)-2,6-dioxo-1,2,3,6-tetrahydropyrimidin-4-yl]-N,N-dimethylformamidine

Product 1

HCID 67025094N'-[3-(2-fluoro-4-iodophenyl)-1-(4-methoxybenzyl)-2,6-dioxo-1,2,3,6-tetrahydropyrimidin-4-yl]-N,N-dimethylformamidineYield 77.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
75 °C

Procedure

To a solution of N′-[3-(2-fluoro-4-iodophenyl)-2,6-dioxo-1,2,3,6-tetrahydropyrimidin-4-yl]-N,N-dimethylformamidine 81 (20.0 g) in N,N-dimethylformamide (150 ml) was added 1,8-diazabicyclo[5.4.0]undec-7-en (14.9 ml) and 4-methoxybenzyl chloride 82 (10.1 ml) at room temperature. The mixture was stirred with heating at 75° C. for 2.5 hrs, 1,8-diazabicyclo[5.4.0]undec-7-en (7.50 ml) and 4-methoxybenzyl chloride (4.00 ml) were added, and the mixture was stirred with heating at the same temperature for 2.5 hrs. After allowing to cool to room temperature, isopropyl alcohol (150 ml) and water (300 ml) were successively added dropwise. The mixture was stirred overnight at room temperature, and the precipitated crystals were collected by filtration and dried to give N′-[3-(2-fluoro-4-iodophenyl)-1-(4-methoxybenzyl)-2,6-dioxo-1,2,3,6-tetrahydropyrimidin-4-yl]-N,N-dimethylformamidine 83 (20.2 g, yield 77.8%) as yellow crystals.

Workup

  1. stirringthe mixture was stirred
  2. temperaturewith heating at the same temperature for 2.5 hrs
  3. temperatureto cool to room temperature
  4. stirringThe mixture was stirred overnight at room temperature
  5. filtrationthe precipitated crystals were collected by filtration
  6. customdried

Sources & evidence

ORD record
ord-854e56356d4e48589b3fcfe5627c560a
Source dataset
uspto-grants-2014_09
Patent number
US08835443B2

Reaction notes

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