Sodium Cyanide → 5-Chloro-4-[(4-chlorophenyl)amino]-6-morpholin-4-ylpyrimidine-2-carbonitrile

HRID 1245420Notes

Reaction equation

HRID 1245420 reaction equation
[C-:1]#[N:2].[Na+].[Cl:4][C:5]1[C:6]([NH:18][C:19]2[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][CH:20]=2)=[N:7][C:8](F)=[N:9][C:10]=1[N:11]1[CH2:16][CH2:15][O:14][CH2:13][CH2:12]1>CS(C)=O>[Cl:4][C:5]1[C:6]([NH:18][C:19]2[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][CH:20]=2)=[N:7][C:8]([C:1]#[N:2])=[N:9][C:10]=1[N:11]1[CH2:16][CH2:15][O:14][CH2:13][CH2:12]1

Participants

4

Reactant 2

HCID 8929Sodium CyanideHCID 219124595-chloro-N-(4-chlorophenyl)-2-fluoro-6-morpholin-4-ylpyrimidin-4-amine

Product 1

HCID 99751475-Chloro-4-[(4-chlorophenyl)amino]-6-morpholin-4-ylpyrimidine-2-carbonitrile

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Sodium cyanide (0.057 g) was added to a solution of the product from step (ii) (0.2 g) in dimethylsulphoxide (5 ml) and the mixture stirred at room temperature. After 18 h, the mixture was partitioned between ethyl acetate and water, the organics separated, washed with water, dried (MgSO4) and evaporated under reduced pressure. The residue was purified by chromatography on silica eluting with 5% ethyl acetate in toluene. Yield 0.09 g

Workup

  1. customthe mixture was partitioned between ethyl acetate and water
  2. washthe organics separated, washed with water
  3. dry with materialdried (MgSO4)
  4. customevaporated under reduced pressure
  5. customThe residue was purified by chromatography on silica eluting with 5% ethyl acetate in toluene

Sources & evidence

ORD record
ord-9b1c15c5dfed432f9e2848d9e640daaa
Source dataset
uspto-grants-2006_10
Patent number
US07125881B2

Reaction notes

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