6-Chloro-N~4~,N~4~-dimethylpyrimidine-2,4-diamine → HCID 58504374, compound

HRID 2367207Notes

Reaction equation

HRID 2367207 reaction equation
[F:1][C:2]1[CH:3]=[C:4](B(O)O)[CH:5]=[C:6]([F:10])[C:7]=1[CH:8]=[O:9].Cl[C:15]1[N:20]=[C:19]([NH2:21])[N:18]=[C:17]([N:22]([CH3:24])[CH3:23])[CH:16]=1>CCOC(C)=O>[NH2:21][C:19]1[N:20]=[C:15]([C:4]2[CH:3]=[C:2]([F:1])[C:7]([CH:8]=[O:9])=[C:6]([F:10])[CH:5]=2)[CH:16]=[C:17]([N:22]([CH3:24])[CH3:23])[N:18]=1

Participants

4

Reactant 2

HCID 2517356-Chloro-N~4~,N~4~-dimethylpyrimidine-2,4-diamineHCID 162177083,5-Difluoro-4-formylphenylboronic acid

Product 1

HCID 58504374HCID 58504374, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

The title compound was prepared following the General Procedure A using: (3,5-difluoro-4-formylphenyl)boronic acid (2.37 g, 12.8 mmol) and 6-chloro-N4,N4-dimethyl-2,4-pyrimidinediamine (2.2 g, 12.8 mmol). The solid was dissolved in EtOAc and precipitated with hexanes. The resulting solid was collected via vacuum filtration to afford the title compound (2.82 g, 80%) as a yellow solid. LC-MS (ES) m/z=279 [M+H]+.

Workup

  1. customThe title compound was prepared
  2. customprecipitated with hexanes
  3. filtrationThe resulting solid was collected via vacuum filtration

Sources & evidence

ORD record
ord-70a2ee2b89f1414c84b29acd83ab527d
Source dataset
uspto-grants-2014_04
Patent number
US08697685B2

Reaction notes

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