Sodium hydride → HCID 86596304, compound

HRID 2117646Notes

Reaction equation

HRID 2117646 reaction equation
[H-].[Na+].[Cl:3][C:4]1[N:9]=[C:8](Cl)[CH:7]=[CH:6][N:5]=1.[N:11]1[CH:16]=[CH:15][CH:14]=[C:13]([CH2:17][O:18][C:19](=[O:29])[NH:20][C:21]2[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][CH:22]=2)[CH:12]=1>CN(C=O)C.[Cl-].[NH4+].C(OCC)(=O)C>[N:11]1[CH:16]=[CH:15][CH:14]=[C:13]([CH2:17][O:18][C:19](=[O:29])[N:20]([C:8]2[CH:7]=[CH:6][N:5]=[C:4]([Cl:3])[N:9]=2)[C:21]2[CH:22]=[CH:23][C:24]([O:27][CH3:28])=[CH:25][CH:26]=2)[CH:12]=1

Participants

7

Reactant 3

HCID 24758Sodium hydrideHCID 775312,4-DichloropyrimidineHCID 69204374HCID 69204374, compound

Product 1

HCID 86596304HCID 86596304, compound

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolventHCID 25517Ammonium ChlorideSolvent

Procedure

Sodium hydride (60% dispersion, 0.30 g, 0.75 mmol) was added to a solution of 2,4-dichloropyrimidine (0.75 g, 0.50 mmol) and (4-methoxyphenyl)-carbamic acid pyridin-3-ylmethyl ester (1.3 g, 0.50 mmol) in DMF (5 mL). The mixture was allowed to stir at room temperature for 2 h. The resulting solution was diluted with sat. aqueous ammonium chloride and ethyl acetate. The organic phase was separated and washed with brine, dried over anhydrous magnesium sulfate, filtered, and concentrated to afford a colorless oil. This oil was purified via column chromatography on silica gel (gradient elution with 0-5% methanol-dichloro-methane) to afford (2-chloropyrimidin-4-yl)-(4-methoxyphenyl)carbamic acid pyridin-3-ylmethyl ester as a tan solid. MS (MH+) 371; Calculated 370.8 for C18H15ClN4O3.

Workup

  1. customThe organic phase was separated
  2. washwashed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto afford a colorless oil
  7. customThis oil was purified via column chromatography on silica gel (gradient elution with 0-5% methanol-dichloro-methane)

Sources & evidence

ORD record
ord-1068acab4de246d79cbf3963a768534c
Source dataset
uspto-grants-2008_10
Patent number
US07442698B2

Reaction notes

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