4-Fluorobenzylamine → HCID 54712022, compound

HRID 1161916Notes

Reaction equation

HRID 1161916 reaction equation
[CH3:1][O:2][CH:3]([O:26][CH3:27])[CH2:4][C:5]1[N:6]([CH3:25])[C:7](=[O:24])[C:8]([O:15]C(=O)C2C=CC=CC=2)=[C:9]([C:11]([O:13]C)=O)[N:10]=1.COC(OC)CC#N.[F:36][C:37]1[CH:44]=[CH:43][C:40]([CH2:41][NH2:42])=[CH:39][CH:38]=1>CO>[CH3:27][O:26][CH:3]([O:2][CH3:1])[CH2:4][C:5]1[N:6]([CH3:25])[C:7](=[O:24])[C:8]([OH:15])=[C:9]([C:11]([NH:42][CH2:41][C:40]2[CH:43]=[CH:44][C:37]([F:36])=[CH:38][CH:39]=2)=[O:13])[N:10]=1

Participants

5

Reactant 3

HCID 673264-FluorobenzylamineHCID 937313,3-DimethoxypropiononitrileHCID 17961879HCID 17961879, compound

Product 1

HCID 54712022HCID 54712022, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Methyl 2-(2,2-dimethoxyethyl)-5-benzoyloxy-1-methyl-6-oxo-1,6-dihydropyrimidine-4-carboxylate (1.0 eq.) (prepared from 3,3-dimethoxypropionitrile by procedure similar to those set forth in Examples 1 or 2) in dry MeOH was treated with 4-fluorobenzyl amine (2.5 eq.) at reflux for 2 hours. Solvent was removed in vacuo and residue triturated with Et2O to obtain the title product.

Workup

  1. temperatureat reflux for 2 hours
  2. customSolvent was removed in vacuo and residue
  3. customtriturated with Et2O

Sources & evidence

ORD record
ord-a3985ab9b9504d118b014d2e6433e624
Source dataset
uspto-grants-2010_10
Patent number
US07820660B2

Reaction notes

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