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tert-Butanol → (2-Methylsulfanyl-4-o-tolyl-pyrimidin-5-yl)-carbamic acid tert.-butyl ester

HRID 650637
Notes
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Reaction equation

HRID 650637 reaction equation
[CH3:1][S:2][C:3]1[N:8]=[C:7]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[CH3:15])[C:6](C(O)=O)=[CH:5][N:4]=1.C([N:21]([CH2:24]C)CC)C.[C:26]([OH:30])([CH3:29])([CH3:28])[CH3:27].C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:38])C=CC=CC=1>C1COCC1>[C:26]([O:30][C:24](=[O:38])[NH:21][C:6]1[C:7]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[CH3:15])=[N:8][C:3]([S:2][CH3:1])=[N:4][CH:5]=1)([CH3:29])([CH3:28])[CH3:27]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 6386tert-ButanolHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 217124342-Methylsulfanyl-4-o-tolyl-pyrimidine-5-carboxylic acid

Product 1

HCID 20677557(2-Methylsulfanyl-4-o-tolyl-pyrimidin-5-yl)-carbamic acid tert.-butyl esterYield 65.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2.33 g (8.95 mmol) 2-methylsulfanyl-4-o-tolyl-pyrimidine-5-carboxylic acid, 1.25 ml triethylamine (8.95 mmol) and 1.68 ml (17.9 mmol) t-butanol in 30 ml THF, 1.97 ml (8.95 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 aqueous phase was extracted twice with CH2Cl2. The combined organic layers were dried (Na2SO4), filtered and evaporated. The residue was purified by chromatography (SiO2, CH2Cl2/ethyl acetate 15:1) to give 1.95 g (65%) (2-methylsulfanyl-4-o-tolyl-pyrimidin-5-yl)-carbamic acid tert.-butyl ester as a colorless solid, MS (TSP): 331 (M+).

Workup

  1. temperaturethe resulting solution heated
  2. temperatureat reflux for 12 hrs
  3. customAfter evaporation of the solvent
  4. extractionThe aqueous phase was extracted twice with 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 15:1)

Sources & evidence

ORD record
ord-c6a7bb57e1334be6b70076fa9b7f9c31
Source dataset
uspto-grants-2001_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06274588B1

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes