Acetic Acid → 2-bromo-N-(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl-N'-methylbenzenesulfonimidamide

HRID 978963Notes

Reaction equation

HRID 978963 reaction equation
N12CCCN=C1CCCCC2.[Br:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[S:19](=[N:22][CH3:23])([NH2:21])=[O:20].[CH3:24][O:25][C:26]1[CH:31]=[C:30]([O:32][CH3:33])[N:29]=[C:28]([NH:34][C:35](=[O:43])OC2C=CC=CC=2)[N:27]=1.C(O)(=O)C>C(#N)C.ClCCl>[Br:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[S:19](=[N:22][CH3:23])([NH:21][C:35]([NH:34][C:28]1[N:29]=[C:30]([O:32][CH3:33])[CH:31]=[C:26]([O:25][CH3:24])[N:27]=1)=[O:43])=[O:20]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 10945667Carbamic acid, N-(4,6-dimethoxy-2-pyrimidinyl)-, phenyl esterHCID 139209002-bromo-N'-methylbenzenesulfonimidamide

Product 1

HCID 139209012-bromo-N-(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl-N'-methylbenzenesulfonimidamideYield 104.6%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Procedure

1,8-Diazabicyclo[5.4.0]undec-7-ene (0.15 mL, 1.0 mmol) was added dropwise over one minute to a stirred solution of 2-bromo-N'-methylbenzenesulfonimidamide (0.25 g, 1.0 mmol) and phenyl (4.6-dimethoxypyrimidin-2-yl)carbamate (0.28 g, 1.0 mmol) in dry acetonitrile (5 mL) at room temperature. The solvent was evaporated, and the residue was dissolved in dichloromethane. Evaporation of this solvent left a pale yellow viscous oil (0.65 g). This was dissolved in CH2Cl2, and acetic acid (57 μL, 1.0 mol) was added. This solution was chromatographed on a column of silica gel using 1:1 dichloromethane-ether as eluant. Fractions containing the product were diluted with toluene. The solvent was evaporated leaving an oil. This was dissolved in dichloromethane, and the solvent was evaporated leaving 2-bromo-N-(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl-N'-methylbenzenesulfonimidamide as a hard amorphous foam (0.45 g) melting at 120°-125° C.

Workup

  1. customThe solvent was evaporated
  2. dissolutionthe residue was dissolved in dichloromethane
  3. customEvaporation of this solvent
  4. waitleft a pale yellow viscous oil (0.65 g)
  5. dissolutionThis was dissolved in CH2Cl2
  6. customThis solution was chromatographed on a column of silica gel using 1:1 dichloromethane-ether as eluant
  7. additionFractions containing the product
  8. additionwere diluted with toluene
  9. customThe solvent was evaporated
  10. customleaving an oil
  11. customthe solvent was evaporated

Sources & evidence

ORD record
ord-41335e220e814cf6a02d6322d971b92c
Source dataset
uspto-grants-1987_05
Patent number
US04666506

Reaction notes

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