p-Tolunitrile → HCID 54689735, compound

HRID 2114754Notes

Reaction equation

HRID 2114754 reaction equation
CC(C)(C)C([O:5][C:6]1[C:11](=[O:12])[N:10]([CH3:13])[C:9]([C:14]2[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][CH:15]=2)=[N:8][C:7]=1[C:21]([O:23]C)=O)=O.CC1C=CC(C#N)=CC=1.[F:36][C:37]1[CH:44]=[CH:43][C:40]([CH2:41][NH2:42])=[CH:39][CH:38]=1>CN(CC1C=C(CN(C)C)C(O)=C(CN(C)C)C=1)C>[F:36][C:37]1[CH:44]=[CH:43][C:40]([CH2:41][NH:42][C:21]([C:7]2[N:8]=[C:9]([C:14]3[CH:15]=[CH:16][C:17]([CH3:20])=[CH:18][CH:19]=3)[N:10]([CH3:13])[C:11](=[O:12])[C:6]=2[OH:5])=[O:23])=[CH:39][CH:38]=1

Participants

5

Reactant 3

HCID 7724p-TolunitrileHCID 673264-FluorobenzylamineHCID 17961704HCID 17961704, compound

Product 1

HCID 54689735HCID 54689735, compound

Reagents, catalysts & solvents 1

HCID 70262,4,6-Tris((dimethylamino)methyl)phenolSolvent

Conditions

Temperature
90 °C

Procedure

To a stirred solution of methyl 5-[(2,2-dimethylpropanoyl)oxy]-1-methyl-2-(4-methylphenyl)-6-oxo-1,6-dihydropyrimidine-4-carboxylate (prepared from 4-methylbenzonitrile by procedures similar to those set forth in Examples 2 or 3) in DMF 3 equivalents of 4-fluorobenzylamine were added and mixture was stirred at 90° C. for 2 h. The title product precipitated from the cooled reaction mixture after the addition of 2 N HCl, and was collected by filtration and washed with diethyl ether.

Workup

  1. additionwere added
  2. customThe title product precipitated from the cooled reaction mixture
  3. additionafter the addition of 2 N HCl
  4. filtrationwas collected by filtration
  5. washwashed with diethyl ether

Sources & evidence

ORD record
ord-fcce6d5863f9414cb9b7207977ed9184
Source dataset
uspto-grants-2008_10
Patent number
US07435734B2

Reaction notes

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