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

HRID 1617248Notes

Reaction equation

HRID 1617248 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 68413953N4-Butyl-5-(4-(chloromethyl)-2-methoxybenzyl)-6-methylpyrimidine-2,4-diamine

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-83fc484fdb26402f93d4549e16168c85
Source dataset
uspto-grants-2014_07
Patent number
US08765939B2

Reaction notes

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