Potassium Cyanide → HCID 58016841, compound

HRID 1926876Notes

Reaction equation

HRID 1926876 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[C:17]3[C:16]([NH:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25]S([O-])(=O)=O)=[N:15][CH:14]=[N:13][C:12]=3[O:11][C:10]=2[C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)=[CH:5][CH:4]=1.[C-]#[N:37].[K+]>CN(C=O)C.C(OCC)(=O)C>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[C:17]3[C:16]([NH:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][C:25]#[N:37])=[N:15][CH:14]=[N:13][C:12]=3[O:11][C:10]=2[C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)=[CH:5][CH:4]=1

Participants

5

Reactant 2

HCID 9032Potassium CyanideHCID 86637367HCID 86637367, compound

Product 1

HCID 58016841HCID 58016841, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Stir a mixture of 400 mg (approx. 0.80 mmol) 6-{[5-(4-methoxyphenyl)-6-phenylfuro[2,3-d]-pyrimidin-4-yl]amino}hexyl-methanesulphonate and 526 mg (8.1 mmol) potassium cyanide in 20 ml DMF overnight at 80° C. After cooling, dilute with ethyl acetate and wash with water and saturated sodium chloride solution. Dry the organic phase over magnesium sulphate and concentrate by evaporation. Purify the raw product by RP-HPLC (column: Gromsil 250 mm×40 mm, 10 μm; acetonitrile/water gradient: 0-3 min 5% acetonitrile, 3-50 min 5%→98% acetonitrile, 50-55 min 98% acetonitrile). 249 mg (72% of theor.) of the title compound is obtained as a yellowish oil.

Workup

  1. temperatureAfter cooling
  2. washwash with water and saturated sodium chloride solution
  3. dry with materialDry the organic phase over magnesium sulphate
  4. concentrationconcentrate by evaporation
  5. customPurify the raw product by RP-HPLC (column: Gromsil 250 mm×40 mm, 10 μm; acetonitrile/water gradient: 0-3 min 5% acetonitrile, 3-50 min 5%→98% acetonitrile, 50-55 min 98% acetonitrile)

Sources & evidence

ORD record
ord-8ac32140faaf485abbe9085fcb27b114
Source dataset
uspto-grants-2012_05
Patent number
US08183246B2

Reaction notes

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