Sodium hydride → (4-Benzyloxy-3,5-dimethyl-phenyl)-(6-chloro-pyrimidin-4-yl)-methanone

HRID 469298Notes

Reaction equation

HRID 469298 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6](Cl)[N:5]=[CH:4][N:3]=1.[CH2:9]([O:16][C:17]1[C:24]([CH3:25])=[CH:23][C:20]([CH:21]=[O:22])=[CH:19][C:18]=1[CH3:26])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.[I-].C[N+]1C2C=CC=CC=2N(C)C=1.[H-].[Na+]>C1COCC1>[CH2:9]([O:16][C:17]1[C:18]([CH3:26])=[CH:19][C:20]([C:21]([C:6]2[CH:7]=[C:2]([Cl:1])[N:3]=[CH:4][N:5]=2)=[O:22])=[CH:23][C:24]=1[CH3:25])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 709434,6-DichloropyrimidineHCID 5635574-(Benzyloxy)-3,5-dimethylbenzaldehydeHCID 118217931,3-Dimethyl-1H-benzimidazol-3-ium iodide

Product 1

HCID 58181140(4-Benzyloxy-3,5-dimethyl-phenyl)-(6-chloro-pyrimidin-4-yl)-methanone

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

150 mg (1.00 mmol) 4,6-dichloropyrimidine, 367 mg (1.50 mmol) 4-benzyloxy-3,5-dimethylbenzaldehyde and 166 mg (0.600 mmol) 1,3-dimethyl-3H-benzimidazol-1-ium-iodide (Chem. Pharm. Bull. 1990, 1147-52) in 10.0 mL THF were stirred at RT. Then 73.0 mg (1.51 mmol) sodium hydride (50% in mineral oil) were added and the reaction mixture was refluxed for 2.5 h. The reaction mixture was added to ice water and extracted with DCM. The organic phase was dried and evaporated down.

Workup

  1. temperaturethe reaction mixture was refluxed for 2.5 h
  2. extractionextracted with DCM
  3. customThe organic phase was dried
  4. customevaporated down

Sources & evidence

ORD record
ord-2b99befe98664d19803e34af9b5504b7
Source dataset
uspto-grants-2014_01
Patent number
US08629137B2

Reaction notes

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