Phenyl chloroformate → HCID 59508950, compound

HRID 1020078Notes

Reaction equation

HRID 1020078 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[N:14]=[CH:13][N:12]=[C:11]([NH2:15])[CH:10]=1.CCN(C(C)C)C(C)C.Cl[C:26](OC1C=CC=CC=1)=[O:27].[CH3:35][N:36]([CH3:40])[CH2:37][CH2:38][NH2:39]>ClCCl>[CH3:35][N:36]([CH3:40])[CH2:37][CH2:38][NH:39][C:26]([NH:15][C:11]1[CH:10]=[C:9]([C:4]2[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=2[O:2][CH3:1])[N:14]=[CH:13][N:12]=1)=[O:27]

Participants

6

Reactant 4

HCID 15891Phenyl chloroformateHCID 66053N,N-DimethylethylenediamineHCID 81531DiisopropylethylamineHCID 497584396-(2-Methoxyphenyl)pyrimidin-4-amine

Product 1

HCID 59508950HCID 59508950, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 6-(2-methoxy-phenyl)-pyrimidin-4-ylamine (XXIV) (0.400 g, 1.98 mmol) and DIPEA (0.300 g, 2.38 mmol) in dry dichloromethane (10 ml) was added phenyl chloroformate (0.370 g, 1.98 mmol) dropwise at −78° C. The reaction mixture was then allowed to stir for 16 hours at room temperature. Dichloromethane was evaporated and the residue was dissolved in 1,4-dioxane (15 ml). N,N-dimethylethylenediamine (L) (0.160 g, 1.98 mmol) was added and the mixture was refluxed for 14 hours. The solvent was evaporated and the crude product was re-dissolved in ethyl acetate, washed with water (2×50 ml) and brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The obtained crude solid product was further purified by silica gel column chromatography (15% methanol/dichloromethane) yielding 1-(2-dimethylamino-ethyl)-3-[6-(2-methoxy-phenyl)-pyrimidin-4-yl]-urea. Yield: 293 mg, 47%.

Workup

  1. customDichloromethane was evaporated
  2. dissolutionthe residue was dissolved in 1,4-dioxane (15 ml)
  3. temperaturethe mixture was refluxed for 14 hours
  4. customThe solvent was evaporated
  5. dissolutionthe crude product was re-dissolved in ethyl acetate
  6. washwashed with water (2×50 ml) and brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customThe obtained crude solid product
  10. customwas further purified by silica gel column chromatography (15% methanol/dichloromethane)

Sources & evidence

ORD record
ord-44a22608c9934267a31d09d750639a64
Source dataset
uspto-grants-2014_05
Patent number
US08716296B2

Reaction notes

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