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

HRID 2387901Notes

Reaction equation

HRID 2387901 reaction equation
[C-:1]#[N:2].[K+].[CH2:4]([NH:8][C:9]1[C:14]([CH2:15][C:16]2[CH:21]=[CH:20][C:19]([CH2:22]Cl)=[CH:18][C:17]=2[O:24][CH3:25])=[C:13]([CH3:26])[N:12]=[C:11]([NH2:27])[N:10]=1)[CH2:5][CH2:6][CH3:7]>CN(C=O)C.CS(C)=O.CCOC(C)=O.C([O-])(O)=O.[Na+]>[NH2:27][C:11]1[N:10]=[C:9]([NH:8][CH2:4][CH2:5][CH2:6][CH3:7])[C:14]([CH2:15][C:16]2[CH:21]=[CH:20][C:19]([CH2:22][C:1]#[N:2])=[CH:18][C:17]=2[O:24][CH3:25])=[C:13]([CH3:26])[N:12]=1

Participants

7

Reactant 2

HCID 9032Potassium CyanideHCID 68413953HCID 68413953, compound

Product 1

HCID 689572822-(4-((2-Amino-4-(butylamino)-6-methylpyrimidin-5-yl)methyl)-3-methoxyphenyl)acetonitrile

Reagents, catalysts & solvents 4

HCID 679Dimethyl SulfoxideSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolventHCID 516892Sodium BicarbonateSolvent

Procedure

KCN (0.844 g) was added to a stirred solution of the product from step (iv) (2.78 g) in DMF (10 mL) and DMSO (10 mL). The mixture was stirred at rt for 15 h. The reaction mixture was diluted with EtOAc (100 mL) and sat. NaHCO3 (100 mL). The organic phase was separated, dried and solvent removed to give the subtitle compound as a solid, 2.2 g.

Workup

  1. customThe organic phase was separated
  2. customdried
  3. customsolvent removed

Sources & evidence

ORD record
ord-9a751211310d4292a8505e0d8ae4503c
Source dataset
uspto-grants-2012_09
Patent number
US08268990B2

Reaction notes

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