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

HRID 1617173

Reaction equation

HRID 1617173 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-7d13fb8c3de64bdaa52c665c53a1211a
Source dataset
uspto-grants-2014_07
Patent number
US08765939B2

Linked notes

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