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Sodium hydride → Carbamic acid, N-[[4-[(4,6-dichloro-2-pyrimidinyl)oxy]phenyl]methyl]-, 1,1-dimethylethyl ester

HRID 1403129
Notes
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Reaction equation

HRID 1403129 reaction equation
[H-].[Na+].[OH:3][C:4]1[CH:18]=[CH:17][C:7]([CH2:8][NH:9][C:10](=[O:16])[O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[CH:6][CH:5]=1.[Cl:19][C:20]1[CH:25]=[C:24]([Cl:26])[N:23]=[C:22](S(C)(=O)=O)[N:21]=1.[Cl-].[NH4+]>COCCOC>[C:12]([O:11][C:10](=[O:16])[NH:9][CH2:8][C:7]1[CH:17]=[CH:18][C:4]([O:3][C:22]2[N:23]=[C:24]([Cl:26])[CH:25]=[C:20]([Cl:19])[N:21]=2)=[CH:5][CH:6]=1)([CH3:14])([CH3:15])[CH3:13]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 2396854,6-Dichloro-2-(methylsulfonyl)pyrimidineHCID 11085418tert-butyl 4-hydroxybenzylcarbamate

Product 1

HCID 101043327Carbamic acid, N-[[4-[(4,6-dichloro-2-pyrimidinyl)oxy]phenyl]methyl]-, 1,1-dimethylethyl ester

Reagents, catalysts & solvents 1

HCID 8071
1,2-Dimethoxyethane
Solvent

Procedure

60% Sodium hydride (394 mg) was suspended in 1,2-dimethoxyethane (20 mL), and tert-butyl 4-hydroxybenzylcarbamate (1 g) and 15-crown-5-ether (1.09 g) were added thereto, followed by stirring at room temperature for 30 minutes. 4,6-Dichloro-2-(methylsulfonyl)pyrimidine was added thereto, followed by stirring at 80° C. overnight. The reaction solution was cooled to room temperature and then an aqueous ammonium chloride solution (50 mL) was added thereto, followed by extraction with ethyl acetate. The extracts were washed with water and saturated brine, and the organic layer was dried over anhydrous magnesium sulfate. The desiccant was removed by filtration and the solvent was evaporated under reduced pressure. The residue was purified using silica gel column chromatography (hexane:ethyl acetate=95:5-85:15) to obtain tert-butyl{-4-[(4,6-dichloropyrimidin-2-yl)oxy]benzyl}carbamate (762 mg).

Workup

  1. stirringby stirring at 80° C. overnight
  2. temperatureThe reaction solution was cooled to room temperature
  3. extractionfollowed by extraction with ethyl acetate
  4. washThe extracts were washed with water and saturated brine
  5. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
  6. customThe desiccant was removed by filtration
  7. customthe solvent was evaporated under reduced pressure
  8. customThe residue was purified

Sources & evidence

ORD record
ord-872eda49922a4c1d933d6d5a435ca04b
Source dataset
uspto-grants-2014_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08912180B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes