tert-Butanol → Tert-butyl{2-[(3-chlorophenyl)amino]-4-(trifluoromethyl)pyrimidin-5-yl}carbamate

HRID 38791

Reaction equation

HRID 38791 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:8][C:9]2[N:14]=[C:13]([C:15]([F:18])([F:17])[F:16])[C:12](C(O)=O)=[CH:11][N:10]=2)[CH:5]=[CH:6][CH:7]=1.C([N:24](CC)CC)C.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=O)C=CC=CC=1.[C:46](=[O:49])([O-])[OH:47].[Na+].[C:51](O)([CH3:54])([CH3:53])[CH3:52]>>[Cl:1][C:2]1[CH:3]=[C:4]([NH:8][C:9]2[N:14]=[C:13]([C:15]([F:16])([F:17])[F:18])[C:12]([NH:24][C:46](=[O:49])[O:47][C:51]([CH3:54])([CH3:53])[CH3:52])=[CH:11][N:10]=2)[CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 5

HCID 6386tert-ButanolHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 516892Sodium BicarbonateHCID 167196552-(3-Chlorophenylamino)-4-trifluoromethylpyrimidine-5-carboxylic acid

Product 1

HCID 68404320Tert-butyl{2-[(3-chlorophenyl)amino]-4-(trifluoromethyl)pyrimidin-5-yl}carbamate

Conditions

Temperature
90 °C

Procedure

To a mixture of 2-[(3-chlorophenyl)amino]-4-(trifluoromethyl)pyrimidine-5-carboxylic acid (307 mg), triethylamine (162 μL), and tert-butyl alcohol (9 mL) was added diphenylphosphorylazide (250 μL), followed by stirring at 90° C. for 7 hours. To the reaction mixture was added a saturated aqueous sodium hydrogen carbonate solution (50 mL), followed by extraction with ethyl acetate (50 mL), and then the extract was washed with saturated brine (30 mL). The organic layer was dried over anhydrous magnesium sulfate and then concentrated under reduced pressure, and the obtained residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate) to obtain tert-butyl {2-[(3-chlorophenyl)amino]-4-(trifluoromethyl)pyrimidin-5-yl}carbamate (270 mg) as a pale yellow powder.

Workup

  1. extractionfollowed by extraction with ethyl acetate (50 mL)
  2. washthe extract was washed with saturated brine (30 mL)
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customthe obtained residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate)

Sources & evidence

ORD record
ord-cc9395f6678a4328bd0405ccf8eb2dbe
Source dataset
uspto-grants-2013_09
Patent number
US08524727B2

Linked notes

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