Water → HCID 59717140, compound

HRID 75675Notes

Reaction equation

HRID 75675 reaction equation
[BH4-].[Na+].[F:3][C:4]1[CH:9]=[C:8]([I:10])[CH:7]=[CH:6][C:5]=1[N:11]1[C:16]([N:17]=[CH:18]N(C)C)=[CH:15][C:14](=[O:22])[N:13]([CH2:23][C:24]2[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[CH:26][CH:25]=2)[C:12]1=[O:32].O.[Cl-].[NH4+]>C(O)(C)(C)C.C(O)C>[F:3][C:4]1[CH:9]=[C:8]([I:10])[CH:7]=[CH:6][C:5]=1[N:11]1[C:16]([NH:17][CH3:18])=[CH:15][C:14](=[O:22])[N:13]([CH2:23][C:24]2[CH:25]=[CH:26][C:27]([O:30][CH3:31])=[CH:28][CH:29]=2)[C:12]1=[O:32]

Participants

6

Reactant 4

HCID 962WaterHCID 25517Ammonium ChlorideHCID 4311764Sodium borohydrideHCID 67025094N'-[3-(2-fluoro-4-iodophenyl)-1-(4-methoxybenzyl)-2,6-dioxo-1,2,3,6-tetrahydropyrimidin-4-yl]-N,N-dimethylformamidine

Product 1

HCID 59717140HCID 59717140, compoundYield 93.1%

Reagents, catalysts & solvents 1

HCID 21460813HCID 21460813, compoundSolvent

Procedure

To a suspension of sodium borohydride (326 mg) in t-butanol/ethanol [2:1 (volume ratio), 18.0 ml] was added N′-[3-(2-fluoro-4-iodophenyl)-1-(4-methoxybenzyl)-2,6-dioxo-1,2,3,6-tetrahydropyrimidin-4-yl]-N,N-dimethylformamidine 83 (3.00 g) with stirring at, room temperature. The mixture was stirred at room temperature for 1 hr, and at 65° C. for 2 hrs. With stirring at the same temperature, water (30.0 ml) and ammonium chloride (461 mg) were successively added, and the mixture was stirred to allow to cool to room temperature. The reaction solution was extracted twice with ethyl acetate. The organic layers were combined, washed successively with saturated aqueous hydrogen carbonate solution and brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The obtained crude product was purified by column chromatography to give 1-(2-fluoro-4-iodophenyl)-3-(4-methoxybenzyl)-6-methylamino-1H-pyrimidine-2,4-dione 84 (2.57 g, yield 93.1%) as a pale-yellow solid.

Workup

  1. stirringThe mixture was stirred at room temperature for 1 hr
  2. additionwere successively added
  3. stirringthe mixture was stirred
  4. temperatureto cool to room temperature
  5. extractionThe reaction solution was extracted twice with ethyl acetate
  6. washwashed successively with saturated aqueous hydrogen carbonate solution and brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customThe obtained crude product
  10. customwas purified by column chromatography

Sources & evidence

ORD record
ord-ad901b4e06fd453b9179fce35ebe3918
Source dataset
uspto-grants-2014_09
Patent number
US08835443B2

Reaction notes

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