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

HRID 1617165Notes

Reaction equation

HRID 1617165 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]([F:27])[CH:7]=1>CS(C)=O.CN(C=O)C.CCOC(C)=O>[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[F:27])=[C:12]([NH:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])[N:13]=1

Participants

6

Reactant 2

HCID 9032Potassium CyanideHCID 689525035-(4-(Chloromethyl)-2-fluorobenzyl)-6-methyl-N4-pentylpyrimidine-2,4-diamine

Product 1

HCID 684148972-(4-((2-Amino-4-methyl-6-(pentylamino)pyrimidin-5-yl)methyl)-3-fluorophenyl)acetonitrileYield 64.1%

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Potassium cyanide (0.473 g) was added to a stirred solution of the product from step (vi) (0.85 g) in DMSO (10 mL) and DMF (10 mL). The mixture was stirred at rt for 15 h, diluted with EtOAc, washed with saturated NaHCO3 solution, saturated brine dried, filtered and evaporated. The crude product was purified by chromatography eluting with 0 to 5% MeOH in DCM to afford the subtitle compound as a yellow solid 0.530 g.

Workup

  1. washwashed with saturated NaHCO3 solution, saturated brine
  2. customdried
  3. filtrationfiltered
  4. customevaporated
  5. customThe crude product was purified by chromatography
  6. washeluting with 0 to 5% MeOH in DCM

Sources & evidence

ORD record
ord-c58396bbe3944e639099aaaf25c134dd
Source dataset
uspto-grants-2014_07
Patent number
US08765939B2

Reaction notes

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