Triphenylphosphine → Urea, (2,6-difluorobenzyl)-

HRID 396999

Reaction equation

HRID 396999 reaction equation
BrC1C(=O)[NH:4][C:5](=[O:18])[N:6]([CH2:9][C:10]2[C:15]([F:16])=[CH:14][CH:13]=[CH:12][C:11]=2[F:17])C=1C.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(OC(/N=N/C(OC(C)(C)C)=O)=O)(C)C>C1COCC1>[F:16][C:15]1[CH:14]=[CH:13][CH:12]=[C:11]([F:17])[C:10]=1[CH2:9][NH:6][C:5]([NH2:4])=[O:18]

Participants

5

Reactant 3

HCID 11776TriphenylphosphineHCID 6034084Di-tert-butyl diazene-1,2-dicarboxylateHCID 120945185-Bromo-1-(2,6-difluoro-benzyl)-6-methyl-1H-pyrimidine-2,4-dione

Product 1

HCID 205282Urea, (2,6-difluorobenzyl)-Yield 251.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of N-(t-butyloxycarbonyl)-D-α-alaninol (1.75 g, 10 mmol) in anhydrous THF (15 mL) was treated with 5-bromo-1-(2,6-difluorobenzyl)-6-methyluracil (3.31 g, 10 mmol) and triphenylphosphine (3.15 g, 12 mmol) at ambient temperature, then di-tert-butylazodicarboxylate (2.76 g, 12 mmol) was introduced. The reaction mixture was stirred at ambient temperature for 16 hours and volatiles were evaporated. The residue was partitioned between saturated NaHCO3/H2O and EtOAc. The organic layer was dried (sodium sulfate), evaporated, and purified by flash chromatography (silica, 1:2 EtOAc/hexanes) to give compound 1 (4.69 g, 96.1%), MS (CI) m/z 388.0, 390.0 (MH+-Boc).

Workup

  1. customvolatiles were evaporated
  2. customThe residue was partitioned between saturated NaHCO3/H2O and EtOAc
  3. dry with materialThe organic layer was dried (sodium sulfate)
  4. customevaporated
  5. custompurified by flash chromatography (silica, 1:2 EtOAc/hexanes)

Sources & evidence

ORD record
ord-d0f93e9a497549be86047db0211e50e4
Source dataset
uspto-grants-2003_08
Patent number
US06608197B2

Linked notes

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