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

HRID 1617181Notes

Reaction equation

HRID 1617181 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[F:20])=[C:9]([CH3:21])[N:8]=[C:7]([NH2:22])[N:6]=1>CS(C)=O.CN(C=O)C.CCOC(C)=O>[NH2:22][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[F:20])=[C:9]([CH3:21])[N:8]=1

Participants

6

Reactant 2

HCID 9032Potassium CyanideHCID 866334044-Chloro-5-(4-(chloromethyl)-2-fluorobenzyl)-6-methylpyrimidin-2-amine

Product 1

HCID 866334052-(4-((2-Amino-4-chloro-6-methylpyrimidin-5-yl)methyl)-3-fluorophenyl)acetonitrile

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Potassium cyanide (0.056 g) was added to a stirred solution of the product from step (ii) (0.13 g) in DMSO (imL) and DMF (1 mL). The mixture was stirred at rt for 15 h and then diluted with EtOAc (10 mL). The organic phase was washed with water and brine then dried, filtered and evaporated to give the subtitle compound, 0.12 g.

Workup

  1. washThe organic phase was washed with water and brine
  2. customthen dried
  3. filtrationfiltered
  4. customevaporated

Sources & evidence

ORD record
ord-4c879e1283e440e6b9a638489cfc5533
Source dataset
uspto-grants-2014_07
Patent number
US08765939B2

Reaction notes

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