N,N-Dimethylaniline → 4-Chloro-6-(3-methoxyphenyl)-2-(methylthio)pyrimidine-5-carbonitrile

HRID 1766058Notes

Reaction equation

HRID 1766058 reaction equation
P(Cl)(Cl)([Cl:3])=O.[C:6]([C:8]1[C:9]([C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([O:23][CH3:24])[CH:18]=2)=[N:10][C:11]([S:15][CH3:16])=[N:12][C:13]=1O)#[N:7].CN(C)C1C=CC=CC=1.O>O1CCOCC1>[Cl:3][C:13]1[N:12]=[C:11]([S:15][CH3:16])[N:10]=[C:9]([C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([O:23][CH3:24])[CH:18]=2)[C:8]=1[C:6]#[N:7]

Participants

6

Reactant 4

HCID 949N,N-DimethylanilineHCID 962WaterHCID 24813Phosphorus oxychlorideHCID 178489905HCID 178489905, compound

Product 1

HCID 3558104-Chloro-6-(3-methoxyphenyl)-2-(methylthio)pyrimidine-5-carbonitrile

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
0 °C

Procedure

Phosphorus oxychloride (0.75 ml) was added to a stirred solution of 5-cyano-4-(3-methoxyphenyl)-2-methylthio-6-hydroxy-pyrimidine (example 1a, 305 mg) in dry 1,4-dioxane (1 ml). A drop of N,N-dimethylaniline was added. After 3 h at 80° C., the mixture was cooled to 0° C. in an ice bath and crushed ice was slowly added. After cessation of the exothermic reaction, H2O (3 ml) was added. The solids were collected by filtration and dried in vacuo.

Workup

  1. customcrushed ice
  2. additionwas slowly added
  3. additionwas added
  4. filtrationThe solids were collected by filtration
  5. customdried in vacuo

Sources & evidence

ORD record
ord-22c754240dd747dcbd4811bfcc20cd5f
Source dataset
uspto-grants-2007_06
Patent number
US07229990B2

Reaction notes

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