Sodium hydride → [4-(6-Chloro-pyrimidin-4-yloxy)-3-methyl-phenyl]-carbamic acid benzyl ester

HRID 1993588Notes

Reaction equation

HRID 1993588 reaction equation
[CH2:1]([O:8][C:9](=[O:19])[NH:10][C:11]1[CH:16]=[CH:15][C:14]([OH:17])=[C:13]([CH3:18])[CH:12]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].[Cl:22][C:23]1[CH:28]=[C:27](Cl)[N:26]=[CH:25][N:24]=1>CN(C=O)C>[CH2:1]([O:8][C:9](=[O:19])[NH:10][C:11]1[CH:16]=[CH:15][C:14]([O:17][C:27]2[CH:28]=[C:23]([Cl:22])[N:24]=[CH:25][N:26]=2)=[C:13]([CH3:18])[CH:12]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 709434,6-DichloropyrimidineHCID 68538458benzyl N-(4-hydroxy-3-methylphenyl)carbamate

Product 1

HCID 86605454[4-(6-Chloro-pyrimidin-4-yloxy)-3-methyl-phenyl]-carbamic acid benzyl ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

(4-Hydroxy-3-methyl-phenyl)-carbamic acid benzyl ester (278 mg, 1.08 mmol) and NaH (29 mg, 1.2 mmol) dissolved in DMF (5 mL) are stirred at rt for 15 min. 4,6-Dichloro-pyrimidine (177 mg, 1.19 mmol) dissolved in DMF (5 mL) is added and the reaction solution is stirred for 1 h, concentrated under reduced pressure and flash chromatographed (silica gel, 2.5×60 cm, AcOEt/hexane=1:6): M+H=370.8; Rf (AcOEt/hexane=1:6): 0.31.

Workup

  1. additionis added
  2. stirringthe reaction solution is stirred for 1 h
  3. concentrationconcentrated under reduced pressure and flash
  4. customchromatographed (silica gel, 2.5×60 cm, AcOEt/hexane=1:6)

Sources & evidence

ORD record
ord-c2f09fd509964f8fabbbcd99d56ec7b0
Source dataset
uspto-grants-2010_01
Patent number
US07652022B2

Reaction notes

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