tert-Butanol → HCID 69926284, compound

HRID 1005980Notes

Reaction equation

HRID 1005980 reaction equation
[CH3:1][S:2][C:3]1[N:8]=[C:7]([O:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[CH3:16])[C:6](C(O)=O)=[CH:5][N:4]=1.C([N:22]([CH2:25]C)CC)C.[C:27]([OH:31])([CH3:30])([CH3:29])[CH3:28].C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:39])C=CC=CC=1>C1COCC1>[C:27]([O:31][C:25](=[O:39])[NH:22][C:6]1[C:7]([O:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[CH3:16])=[N:8][C:3]([S:2][CH3:1])=[N:4][CH:5]=1)([CH3:30])([CH3:29])[CH3:28]

Participants

6

Reactant 4

HCID 6386tert-ButanolHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 22674259HCID 22674259, compound

Product 1

HCID 69926284HCID 69926284, compoundYield 357.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1.90 g (6.88 mmol) 2-methylsulfanyl-4-o-tolyloxy-pyrimidine-5-carboxylic acid, 0.95 ml triethylamine (6.88 mmol) and 1.29 ml (1.37 mmol) t-butanol in 25 ml THF, 1.47 ml (6.88 mmol) diphenylphosphorylazide were added and the resulting solution heated at reflux for 12 hrs. After evaporation of the solvent, the residue was distributed between CH2Cl2 and H2O. The aquoeus phase was extracted twice with 80 ml CH2Cl2. The combined organic layers were dried (Na2SO4), filtered and evaporated. The residue was purified by chromatography (SiO2, CH2Cl2, ethyl acetate 40:1) to give 1.70 g (71%) (2-methylsulfanyl-4-o-tolyloxy-pyrimidin-5-yl)-carbamic acid tert.-butyl ester as a colorless solid, MS (ISP): 348.2 (M+H)+.

Workup

  1. temperaturethe resulting solution heated
  2. temperatureat reflux for 12 hrs
  3. customAfter evaporation of the solvent
  4. extractionThe aquoeus phase was extracted twice with 80 ml CH2Cl2
  5. dry with materialThe combined organic layers were dried (Na2SO4)
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue was purified by chromatography (SiO2, CH2Cl2, ethyl acetate 40:1)

Sources & evidence

ORD record
ord-5c566e7128214bab9b9191cbd2f9bcb2
Source dataset
uspto-grants-2004_09
Patent number
US06787539B2

Reaction notes

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