Dimethyl Ether → HCID 178488688, compound

HRID 1296944Notes

Reaction equation

HRID 1296944 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[C:13]([CH3:14])=[N:12][N:11](COCC[Si](C)(C)C)[C:10]=2[C:23]2[CH:28]=[C:27]([CH3:29])[N:26]=[C:25]([NH2:30])[N:24]=2)=[CH:5][CH:4]=1.B(Cl)(Cl)Cl.COC.C([O-])(O)=O.[Na+]>ClCCl>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[C:13]([CH3:14])=[N:12][NH:11][C:10]=2[C:23]2[CH:28]=[C:27]([CH3:29])[N:26]=[C:25]([NH2:30])[N:24]=2)=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 8254Dimethyl EtherHCID 25135Boron TrichlorideHCID 516892Sodium BicarbonateHCID 58913544HCID 58913544, compound

Product 1

HCID 178488688HCID 178488688, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

4-[4-(4-Methoxy-phenyl)-5-methyl-2-(2-trimethylsilanyl-ethoxymethyl)-2H-pyrazol-3-yl]-6-methyl-pyrimidin-2-ylamine was dissolved in anhydrous dichloromethane under nitrogen. 2M borontrichloride.dimethylether in dichloromethane (7 eq) was added dropwise, and all was stirred for 2 hours. The reaction mixture was added dropwise to sat. NaHCO3(aq) and extracted into dichloromethane. The organic phase was dried over MgSO4, filtered and concentrated in vacuo. The residue was purified by preparative LC/MS to give 4-[4-(4-methoxy-phenyl)-5-methyl-2H-pyrazol-3-yl]-6-methyl-pyrimidin-2-ylamine as a solid.

Workup

  1. extractionextracted into dichloromethane
  2. dry with materialThe organic phase was dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by preparative LC/MS

Sources & evidence

ORD record
ord-699526810ae4486ea115bac0841cde0e
Source dataset
uspto-grants-2007_07
Patent number
US07247734B2

Reaction notes

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