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

HRID 2387810Notes

Reaction equation

HRID 2387810 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])=[C:8]([O:27][CH3:28])[CH:7]=1>CS(C)=O.CN(C=O)C.C([O-])(O)=O.[Na+]>[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][C:8]=2[O:27][CH3:28])=[C:12]([NH:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])[N:13]=1

Participants

6

Reactant 2

HCID 9032Potassium CyanideHCID 689586835-(4-(Chloromethyl)-2-methoxybenzyl)-6-methyl-N4-pentylpyrimidine-2,4-diamine

Product 1

HCID 689540842-(4-((2-Amino-4-methyl-6-(pentylamino)pyrimidin-5-yl)methyl)-3-methoxyphenyl)acetonitrileYield 62.2%

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolventHCID 6228DimethylformamideSolventHCID 516892Sodium BicarbonateSolvent

Procedure

Potassium cyanide (0.53 g) was added to a solution of the product from step (vi) (0.99 g) in DMSO (10 mL) and DMF (10 mL) under nitrogen. The resulting mixture was stirred at rt for 20 h and diluted with saturated aqueous NaHCO3 (50 mL). The mixture was extracted with EtOAc and the combined organic phase was washed with water and brine, dried, filtered and evaporated. The crude product was purified by chromatography, eluting with 5% MeOH in DCM to afford the subtitle compound as an orange solid 0.6 g.

Workup

  1. extractionThe mixture was extracted with EtOAc
  2. washthe combined organic phase was washed with water and brine
  3. customdried
  4. filtrationfiltered
  5. customevaporated
  6. customThe crude product was purified by chromatography
  7. washeluting with 5% MeOH in DCM

Sources & evidence

ORD record
ord-94054e7a853e4e02826370c7828f7c78
Source dataset
uspto-grants-2012_09
Patent number
US08268990B2

Reaction notes

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