Sodium Cyanide → HCID 10157189, compound

HRID 1271130Notes

Reaction equation

HRID 1271130 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[C:9]([Cl:11])[CH:10]=1)[N:7]([C:12]1[C:17](I)=[C:16]([NH:19][CH:20]([CH2:23][CH3:24])[CH2:21][CH3:22])[N:15]=[C:14]([CH3:25])[N:13]=1)[CH2:6][CH2:5]2.[C:26]([Cu])#[N:27].[C-]#N.[Na+].[NH4+].[Cl-].[NH4+].[OH-]>CN(C=O)C>[C:26]([C:17]1[C:12]([N:7]2[C:8]3[C:4](=[CH:3][C:2]([Cl:1])=[CH:10][C:9]=3[Cl:11])[CH2:5][CH2:6]2)=[N:13][C:14]([CH3:25])=[N:15][C:16]=1[NH:19][CH:20]([CH2:23][CH3:24])[CH2:21][CH3:22])#[N:27]

Participants

6

Reactant 4

HCID 8929Sodium CyanideHCID 10300102HCID 10300102, compoundHCID 21863491Ammonium chloride ammonium hydroxideHCID 178418546HCID 178418546, compound

Product 1

HCID 10157189HCID 10157189, compoundYield 22.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-(5,7-Dichloro-2,3-dihydro-1H-indol-1-yl)-6-(1-ethylpropylamino)-5-iodo-2-methylpyrimidine (450 mg, 0.92 mmol) was heated at 140° C. in 5 mL DMF with CuCN (111 mg, 1.23 mmol) and NaCN (84 mg, 1.70 mmol) for 6 h. The reaction was poured into 20 mL 9:1 NH4Cl/NH4OH and stirred for 20 min. The product was extracted with EtOAc (100 mL) and the EtOAc was washed with water (20 mL), brine, dried over (MgSO4) and stripped in vacuo. The residue was chromatographed on silica gel using 20% EtOAc/hexanes as eluent to give the title compound 80 mg, mp 163–165° C.

Workup

  1. extractionThe product was extracted with EtOAc (100 mL)
  2. washthe EtOAc was washed with water (20 mL), brine
  3. dry with materialdried over (MgSO4)
  4. customThe residue was chromatographed on silica gel using 20% EtOAc/hexanes as eluent

Sources & evidence

ORD record
ord-1a56fb7eedf8424991e5e771735f50c8
Source dataset
uspto-grants-2007_04
Patent number
US07205306B2

Reaction notes

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