Potassium Cyanide → 2-(4-((2-Amino-4-methyl-6-(pentylamino)pyrimidin-5-yl)methyl)phenyl)acetonitrile

HRID 1617191Notes

Reaction equation

HRID 1617191 reaction equation
[C-:1]#[N:2].[K+].Cl[CH2:5][C:6]1[CH:26]=[CH:25][C:9]([CH2:10][C:11]2[C:12]([NH:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])=[N:13][C:14]([NH2:18])=[N:15][C:16]=2[CH3:17])=[CH:8][CH:7]=1>CS(C)=O.CN(C=O)C>[NH2:18][C:14]1[N:15]=[C:16]([CH3:17])[C:11]([CH2:10][C:9]2[CH:25]=[CH:26][C:6]([CH2:5][C:1]#[N:2])=[CH:7][CH:8]=2)=[C:12]([NH:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])[N:13]=1

Participants

5

Reactant 2

HCID 9032Potassium CyanideHCID 684164415-(4-(Chloromethyl)benzyl)-6-methyl-N4-pentylpyrimidine-2,4-diamine

Product 1

HCID 595906382-(4-((2-Amino-4-methyl-6-(pentylamino)pyrimidin-5-yl)methyl)phenyl)acetonitrile

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 6228DimethylformamideSolvent

Procedure

Potassium cyanide (0.75 g) was added to a solution of the crude product from step (vi) in DMSO (10 ml) and DMF (10 ml). The mixture was stirred at rt for 18 h, then partitioned between EtOAc/water. The organics were separated, washed with aq NaHCO3 solution, dried and evaporated under reduced pressure to afford the subtitle compound, 1.2 g.

Workup

  1. custompartitioned between EtOAc/water
  2. customThe organics were separated
  3. washwashed with aq NaHCO3 solution
  4. customdried
  5. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-4ecd90a9026444e18d50bf8de49e814d
Source dataset
uspto-grants-2014_07
Patent number
US08765939B2

Reaction notes

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