Potassium Cyanide → 2-(4-((2-Amino-4-chloro-6-methylpyrimidin-5-yl)methyl)-3-methoxyphenyl)acetonitrile

HRID 2387827Notes

Reaction equation

HRID 2387827 reaction equation
[C-:1]#[N:2].[K+].[Cl:4][C:5]1[C:10]([CH2:11][C:12]2[CH:17]=[CH:16][C:15]([CH2:18]Cl)=[CH:14][C:13]=2[O:20][CH3:21])=[C:9]([CH3:22])[N:8]=[C:7]([NH2:23])[N:6]=1>CS(C)=O.CN(C=O)C.O>[NH2:23][C:7]1[N:6]=[C:5]([Cl:4])[C:10]([CH2:11][C:12]2[CH:17]=[CH:16][C:15]([CH2:18][C:1]#[N:2])=[CH:14][C:13]=2[O:20][CH3:21])=[C:9]([CH3:22])[N:8]=1

Participants

6

Reactant 2

HCID 9032Potassium CyanideHCID 866334014-Chloro-5-(4-(chloromethyl)-2-methoxybenzyl)-6-methylpyrimidin-2-amine

Product 1

HCID 866334022-(4-((2-Amino-4-chloro-6-methylpyrimidin-5-yl)methyl)-3-methoxyphenyl)acetonitrile

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Potassium cyanide (0.17 g) was added to a stirred solution of the product from step (ii) (0.40 g) in DMSO (5 mL) and DMF (5 mL). The mixture was stirred at rt for 15 h, diluted with water and then extracted with EtOAc. The combined organic phase was dried, filtered and evaporated to give the subtitle compound, 0.20 g.

Workup

  1. extractionextracted with EtOAc
  2. customThe combined organic phase was dried
  3. filtrationfiltered
  4. customevaporated

Sources & evidence

ORD record
ord-37a3a0cf69114922937d217fa2f225fc
Source dataset
uspto-grants-2012_09
Patent number
US08268990B2

Reaction notes

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