Iodoethane → HCID 58016889, compound

HRID 1926930Notes

Reaction equation

HRID 1926930 reaction equation
[CH3:1][O:2][C:3](=[O:32])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][NH:9][C:10]1[C:11]2[C:18]([C:19]3[CH:24]=[CH:23][C:22]([NH2:25])=[CH:21][CH:20]=3)=[C:17]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[O:16][C:12]=2[N:13]=[CH:14][N:15]=1.[CH2:33](N(CC)CC)[CH3:34].C(I)C>C(#N)C.ClCCl>[CH3:1][O:2][C:3](=[O:32])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][NH:9][C:10]1[C:11]2[C:18]([C:19]3[CH:20]=[CH:21][C:22]([NH:25][CH2:33][CH3:34])=[CH:23][CH:24]=3)=[C:17]([C:26]3[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=3)[O:16][C:12]=2[N:13]=[CH:14][N:15]=1

Participants

6

Reactant 3

HCID 6340IodoethaneHCID 8471TriethylamineHCID 58016827HCID 58016827, compound

Product 1

HCID 58016889HCID 58016889, compoundYield 19.9%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Procedure

Put 29.2 mg (0.068 mmol) 6-({5-[4-aminophenyl]-6-phenylfuro[2,3-d]pyrimidin-4-yl}amino)-hexanoic acid methyl ester in 0.5 ml acetonitrile with 14 μl (0.102 mmol) triethylamine and add an excess of ethyl iodide in portions at 45° C. in closed apparatus over a period of 12 h. After cooling, dilute the reaction mixture with dichloromethane, wash successively with satd. sodium hydrogencarbonate solution and satd. sodium chloride solution, dry over sodium sulphate and concentrate by vacuum evaporation. After preparative RP-HPLC (gradient: acetonitrile/water), 6.2 mg of the target compound (19.9% of theor.) is isolated from the raw product mixture.

Workup

  1. temperatureAfter cooling
  2. washwash successively with satd
  3. dry with materialsodium chloride solution, dry over sodium sulphate
  4. concentrationconcentrate by vacuum evaporation

Sources & evidence

ORD record
ord-0b1a427e7e1f442896e5d250030ac8bd
Source dataset
uspto-grants-2012_05
Patent number
US08183246B2

Reaction notes

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